GB1042894A - 3-cyanopyrrolidines - Google Patents

3-cyanopyrrolidines

Info

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
Application number
GB2382563A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
AH Robins Co Inc
Original Assignee
AH Robins Co Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by AH Robins Co Inc filed Critical AH Robins Co Inc
Publication of GB1042894A publication Critical patent/GB1042894A/en
Expired legal-status Critical Current

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

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.
GB2382563A 1962-06-18 1963-06-14 3-cyanopyrrolidines Expired GB1042894A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (1)

* Cited by examiner, † Cited by third party
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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