GB1042894A - 3-cyanopyrrolidines - Google Patents
3-cyanopyrrolidinesInfo
- Publication number
- GB1042894A GB1042894A GB2382563A GB2382563A GB1042894A GB 1042894 A GB1042894 A GB 1042894A GB 2382563 A GB2382563 A GB 2382563A GB 2382563 A GB2382563 A GB 2382563A GB 1042894 A GB1042894 A GB 1042894A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- cyanopyrrolidines
- pyrrolidine
- methyl
- prepared
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Novel 3-cyanopyrrolidines of the formula <FORM:1042894/C2/1> wherein R is hydrogen or an alkyl, dialkyl-aminoalkyl, aralkyl, heterocyclic or alicylic radical and X is hydrogen or an aliphatic, aromatic or alicyclic radical, and salts thereof are prepared by reacting a compound of the formula <FORM:1042894/C2/2> (wherein "Hal" is a halogen atom) with an alkali metal cyanide in the presence of dimethyl sulphoxide and, if desired, further reacting the product in which R is hydrogen with an R-halide (in which R is other than hydrogen) in the presence of a solution of sodamide in ammonia. The above 3-cyanopyrrolidines in which X is other than hydrogen may be hydrogenated to the corresponding 3-aminomethyl-pyrrolidines, converted to the corresponding diazo compounds with nitrous acid and hydrolysed to the corresponding 3-hydroxymethyl-pyrrolidines. 1 - Methyl - 3 - bromo - pyrrolidine, 1 - methyl-3-chloro -pyrrolidine and 1-ethyl-3-chloro-pyrrolidine are prepared by reacting 1-methyl- or 1 -ethyl-3-pyrrolidinol with phosphorus tribromide or trichloride as appropriate. 3-Chloropyrrolidine is prepared by catalytic hydrogenation of 1-benzyl-3-chloropyrrolidine.ALSO:Pharmaceutical and insecticidal compositions contain as cholinesterase inhibitors 3-cyanopyrrolidines of the formula:- <FORM:1042894/A5-A6/1> wherein R is hydrogen or an alkyl, dialkylaminoalkyl, aralkyl, heterocyclic or alicyclic radical and X is hydrogen or an aliphatic, aromatic or alicyclic radical, or salts thereof.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US20297162A | 1962-06-18 | 1962-06-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1042894A true GB1042894A (en) | 1966-09-14 |
Family
ID=22751953
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB2382563A Expired GB1042894A (en) | 1962-06-18 | 1963-06-14 | 3-cyanopyrrolidines |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1269619B (en) |
GB (1) | GB1042894A (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102675179A (en) * | 2012-05-17 | 2012-09-19 | 盛世泰科生物医药技术(苏州)有限公司 | Synthesis method of 3-bromine-1-methyl pyrrolidine |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3923670A1 (en) * | 1988-07-19 | 1990-01-25 | Rainer Buchholz | Machine for fitting stoppers to bottles - incorporates device to attach stopper to bottle with wire clip |
-
1963
- 1963-06-14 GB GB2382563A patent/GB1042894A/en not_active Expired
- 1963-06-18 DE DEP1269A patent/DE1269619B/en active Pending
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102675179A (en) * | 2012-05-17 | 2012-09-19 | 盛世泰科生物医药技术(苏州)有限公司 | Synthesis method of 3-bromine-1-methyl pyrrolidine |
Also Published As
Publication number | Publication date |
---|---|
DE1269619B (en) | 1968-06-06 |
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