GB552065A - Manufacture of heterocyclic bases - Google Patents

Manufacture of heterocyclic bases

Info

Publication number
GB552065A
GB552065A GB1489441A GB1489441A GB552065A GB 552065 A GB552065 A GB 552065A GB 1489441 A GB1489441 A GB 1489441A GB 1489441 A GB1489441 A GB 1489441A GB 552065 A GB552065 A GB 552065A
Authority
GB
United Kingdom
Prior art keywords
methyl
phenyl
benzylamine
carbethoxy
ethyl ester
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
GB1489441A
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.)
ALEXAMDER LANG MORRISON
Roche Products Ltd
Original Assignee
ALEXAMDER LANG MORRISON
Roche Products Ltd
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 ALEXAMDER LANG MORRISON, Roche Products Ltd filed Critical ALEXAMDER LANG MORRISON
Priority to GB1489441A priority Critical patent/GB552065A/en
Publication of GB552065A publication Critical patent/GB552065A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

552,065. Cyanamino and heterocyclic compounds. ROCHE PRODUCTS, Ltd., BERGEL, F., HINDLEY, N. C., MORRISON, A. L., and RINDERKNECHT, H. Nov. 19, 1941, No. 14894. [Class 2 (iii)] Compounds of the formula are prepared by condensing Hal.(CH 2 )n.N (R 1 )CH 2 C 6 H 5 with R 2 (R 3 ).C.(CN)H, where n =2 or 3, R 1 is alkyl or aryl, R 2 is an aryl which may carry substituents not interfering with the reaction, and R 3 3 is hydrogen, alkyl, aryl or carboxylic ester group, in the presence of an alkaline condensing agent such as sodamide. Examples are α - phenyl - y - (methyl - benzylamino) butyronitrile from # - chloroethyl - methyl - benzylamine and phenylacetonitrile, ethyl ester of α - phenyl - α - cyano - y - (benzyl - methyl amino) butyric acid from # - chloroethyl - methyl - benzylamine and phenyl - carbethoxy - acetonitrile, ethyl ester of α - phenyl - α - cyano - 8 - (methyl benzylamino) - valeric acid from y - chloropropyl - methyl - benzylamine and phenyl - carbethoxy - acetonitrile, and ethyl ester of α - (o - tolyl) - α - cyano - 8 - (methyl - benzylamino ) - valeric acid from y - chloropropyl - methyl - benzylamine and o - tolyl - cyanacetic ethyl ester. Pyrrolidine or piperidine bases or derivatives are made by catalytic hydrogenation of the above compounds and making alkaline the hydrogenated reaction mixture. Examples are 1 - methyl - 3 - phenyl - pyrrolidine, 1 - methyl - 3 - phenyl - 3 - carbethoxy pyrrolidine, 1 - methyl - 3 - phenyl - 3 - carbethoxy piperidine, and 1 - methyl - 3 - (o - tolyl) - 3 - carbethoxy piperidine. #- - Chloroethyl methyl benzylamine is prepared by the action of thionyl chloride in chloroform solution on # hydroxy - ethyl - methyl - benzylamine. α - Chloropropyl - methyl - benzylamime is prepared by the action of thionyl chloride on y - hydroxy propylmethyl - benzylamine (by condensing trimethylene chlorhydrin with methylbenzylamine) or by condensing methylbenzylamine with 1 : 3 - chlorobromopropane.
GB1489441A 1941-11-19 1941-11-19 Manufacture of heterocyclic bases Expired GB552065A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1489441A GB552065A (en) 1941-11-19 1941-11-19 Manufacture of heterocyclic bases

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1489441A GB552065A (en) 1941-11-19 1941-11-19 Manufacture of heterocyclic bases

Publications (1)

Publication Number Publication Date
GB552065A true GB552065A (en) 1943-03-22

Family

ID=10049411

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1489441A Expired GB552065A (en) 1941-11-19 1941-11-19 Manufacture of heterocyclic bases

Country Status (1)

Country Link
GB (1) GB552065A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2446804A (en) * 1943-03-09 1948-08-10 Hoffmann La Roche 3-aryl-3-carbalkoxy piperidines and pyrrolidines and synthesis thereof
US2496326A (en) * 1945-06-16 1950-02-07 Winthrop Stearns Inc Production of a 3-(lower acyl) amino-3-carbalkoxy-2-piperidones
US2498435A (en) * 1946-07-08 1950-02-21 Hoffmann La Roche Production of 1,3 dimethyl-4-phenyl-4-hydroxy-piperidine
US2498433A (en) * 1946-07-08 1950-02-21 Hoffmann La Roche 1,3 dimethyl-4-propionoxy-4-phenyl-piperidine and acid addition salts thereof
US2507631A (en) * 1944-01-19 1950-05-16 Ciba Pharm Prod Inc Pyridine and piperidine compounds and process of making same
US2510784A (en) * 1949-01-13 1950-06-06 Sterling Drug Inc Bis (tertiaryaminoalkyl) arylacetonitriles and the corresponding acids and esters
US2542466A (en) * 1947-08-23 1951-02-20 Univ Michigan Cyclohexyl-phenyl-aminoalkylketones and their production

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2446804A (en) * 1943-03-09 1948-08-10 Hoffmann La Roche 3-aryl-3-carbalkoxy piperidines and pyrrolidines and synthesis thereof
US2507631A (en) * 1944-01-19 1950-05-16 Ciba Pharm Prod Inc Pyridine and piperidine compounds and process of making same
US2496326A (en) * 1945-06-16 1950-02-07 Winthrop Stearns Inc Production of a 3-(lower acyl) amino-3-carbalkoxy-2-piperidones
US2498435A (en) * 1946-07-08 1950-02-21 Hoffmann La Roche Production of 1,3 dimethyl-4-phenyl-4-hydroxy-piperidine
US2498433A (en) * 1946-07-08 1950-02-21 Hoffmann La Roche 1,3 dimethyl-4-propionoxy-4-phenyl-piperidine and acid addition salts thereof
US2542466A (en) * 1947-08-23 1951-02-20 Univ Michigan Cyclohexyl-phenyl-aminoalkylketones and their production
US2510784A (en) * 1949-01-13 1950-06-06 Sterling Drug Inc Bis (tertiaryaminoalkyl) arylacetonitriles and the corresponding acids and esters

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