US1795738A - Method of producing substituted guanidines - Google Patents

Method of producing substituted guanidines Download PDF

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Publication number
US1795738A
US1795738A US305863A US30586328A US1795738A US 1795738 A US1795738 A US 1795738A US 305863 A US305863 A US 305863A US 30586328 A US30586328 A US 30586328A US 1795738 A US1795738 A US 1795738A
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producing substituted
substituted guanidines
amine
parts
alpha
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US305863A
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Schotte Herbert
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Schering Kahlbaum AG
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Schering Kahlbaum AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
    • C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines

Definitions

  • My invention refers to the production of guanidine derivatives and more especially to a method of producing substituted guan1- dines.
  • tween dialkyl cyanamides and amine salts is caused to take place very smoothly, and with many derivatives it is not even necessary to increase the temperature.
  • the process of manufacture accordingto the invention is by bringing a dialkyl cyanamide into reaction with an amine salt in the presence of a free amine.
  • hydrohalogen acid salts of which are easily soluble in water and the picrate of;
  • Example 4 The method of producing substituted guanidines by treating a dialkyl cyanamid with a salt of an amine which has at least one hydrogen atom attached to the nitrogen atom, in the presence of the corresponding free amine.
  • Example 1 5 parts of diethyl cyanamide heated with i 6.5 parts of aniline hydrochloride and 3 parts of aniline for 10 hours to 100 C. give alpha, alpha-diethyl-beta-phenyl guanidine which is obtained as the oily base by steam distillation of the deposit after rendering alkaline or which can be separated as the pi'crate of melt-

Description

Patented Mar. ie, 1931 omrsn stares rarer 'FFICE HERBERT scnorrnon nnnmn-nnrnrcxnnnonr, GERMANY, ASSIGNOR 'IO scnnnmo- 1 KAI-ILBAUM A. a, or BERLIN, GERMANY METHOI P OF PRODUCING SUBSTITUTED GUANIDINES No Drawing. Application filed September 13, 1928, Serial No. 305,863, and in Germany September 12, 1927.
My invention refers to the production of guanidine derivatives and more especially to a method of producing substituted guan1- dines. I i
l/Vhereas cyanamide and mono alkyl cyanamides react with amine salts veryf'avourably particularly when working in Very concentrated solution disubstituted cyanamides do not'react favourably with amines or amine salts. (Compare Lecher & Demmler Zeitschrift fur physiologische Chemie 167,170 (1927)). v
' By the present invention the reaction be-,
tween dialkyl cyanamides and amine salts is caused to take place very smoothly, and with many derivatives it is not even necessary to increase the temperature.
The process of manufacture accordingto the invention is by bringing a dialkyl cyanamide into reaction with an amine salt in the presence of a free amine.
The reason for the smooth and favourable reaction cannot yet be, definitely explained, possibly an intermediate product of the following constitution is produced R R \N/ ({X [I NH wherein R is an alkyl and X an acid radical which reacts further with the amine.
The following formula shows the structure of the guanidine nucleus,
are however better in the first case.
ing point 118 C. Aniline itself also reacts with dialkyl cyanamide without the addition of hydrochloride. The yields of guanidine Example 2 2.7 parts of diethyl cyanamide, 5 parts of isoamylamine and 7 parts of isoamylamine hydrochloride give on long standing or after heating for about one hour to 100 C. the alpha, alpha-dlethyLbeta-isoamyl guanidine,
the hydrohalogen acid salts of which are easily soluble in water and the picrate of;
the same manner as in Example 2 (with four parts of amine and live partsof hydrochloride) give alpha alpha-dimethyl-beta-iso-,
The. picrate melts at.
amyl-guanidine Example 4 The method of producing substituted guanidines by treating a dialkyl cyanamid with a salt of an amine which has at least one hydrogen atom attached to the nitrogen atom, in the presence of the corresponding free amine.
HERBERT SCHOTTE.
N511 6 NHfY The following examples illustrate the invention.
' Example 1 5 parts of diethyl cyanamide heated with i 6.5 parts of aniline hydrochloride and 3 parts of aniline for 10 hours to 100 C. give alpha, alpha-diethyl-beta-phenyl guanidine which is obtained as the oily base by steam distillation of the deposit after rendering alkaline or which can be separated as the pi'crate of melt-
US305863A 1927-09-12 1928-09-13 Method of producing substituted guanidines Expired - Lifetime US1795738A (en)

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DE1795738X 1927-09-12

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Cited By (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2425341A (en) * 1944-08-11 1947-08-12 American Cyanamid Co Production of mono- and unsymmetrically disubstituted guanidines
US2446421A (en) * 1944-11-03 1948-08-03 Ici Ltd Manufacture of arylbiguanide hydrochlorides
US2537834A (en) * 1951-01-09 Substituted guanylmelamines
US2898369A (en) * 1956-02-23 1959-08-04 Mcneilab Inc N,n,n',n'' tetraethyl guanidine and its acid addition salts
US5262568A (en) * 1990-03-02 1993-11-16 State Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5312840A (en) * 1986-07-10 1994-05-17 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Substituted guanidines having high binding to the sigma receptor and the use thereof
US5336689A (en) * 1990-03-02 1994-08-09 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5385946A (en) * 1986-07-10 1995-01-31 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Method for treating hypertension with disubstituted granidine compounds
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US6072075A (en) * 1997-05-22 2000-06-06 The Regents Of The University Of California Guanidinylation reagents
US20070265348A1 (en) * 1994-02-03 2007-11-15 Scion Pharmaceuticals, Inc, A Delaware Corporation Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines

Cited By (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2537834A (en) * 1951-01-09 Substituted guanylmelamines
US2425341A (en) * 1944-08-11 1947-08-12 American Cyanamid Co Production of mono- and unsymmetrically disubstituted guanidines
US2446421A (en) * 1944-11-03 1948-08-03 Ici Ltd Manufacture of arylbiguanide hydrochlorides
US2898369A (en) * 1956-02-23 1959-08-04 Mcneilab Inc N,n,n',n'' tetraethyl guanidine and its acid addition salts
US5312840A (en) * 1986-07-10 1994-05-17 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education Substituted guanidines having high binding to the sigma receptor and the use thereof
US5385946A (en) * 1986-07-10 1995-01-31 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Method for treating hypertension with disubstituted granidine compounds
US5604228A (en) * 1986-07-10 1997-02-18 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5478863A (en) * 1986-07-10 1995-12-26 State Of Oregon, Oregon Health Sciences University Of Oregon Substituted guanidines having high binding to the sigma receptor and the use thereof
US5502255A (en) * 1986-07-10 1996-03-26 State Of Oregon Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Substituted guanidines having high binding to the sigma receptor and the use thereof
US5262568A (en) * 1990-03-02 1993-11-16 State Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5336689A (en) * 1990-03-02 1994-08-09 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University And The University Of Oregon Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5559154A (en) * 1990-03-02 1996-09-24 Oregon State Board Of Higher Education Tri- and tetra-substituted guanidines and their use as excitatory amino acid antagonists
US5574070A (en) * 1990-05-25 1996-11-12 State Of Oregon, Acting By And Through The Oregon State Board Of Higher Education, Acting For And On Behalf Of The Oregon Health Sciences University Substituted guanidines having high binding to the sigma receptor and the use thereof
US5403861A (en) * 1991-02-08 1995-04-04 Cambridge Neuroscience, Inc. Substituted guanidines and derivatives thereof as modulators of neurotransmitter release and novel methodology for identifying neurotransmitter release blockers
US5672608A (en) * 1991-02-08 1997-09-30 Cambridge Neuroscience, Inc. Acenaphthyl substituted guanidines and methods of use thereof
US20070265348A1 (en) * 1994-02-03 2007-11-15 Scion Pharmaceuticals, Inc, A Delaware Corporation Therapeutic guanidines
US7351743B1 (en) 1994-02-03 2008-04-01 Wyeth Therapeutic guanidines
US6072075A (en) * 1997-05-22 2000-06-06 The Regents Of The University Of California Guanidinylation reagents
US6380358B1 (en) 1997-05-22 2002-04-30 The Regents Of The University Of California Guanidinylation reagents

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