GB816168A - Tertiary amines - Google Patents

Tertiary amines

Info

Publication number
GB816168A
GB816168A GB29842/57A GB2984257A GB816168A GB 816168 A GB816168 A GB 816168A GB 29842/57 A GB29842/57 A GB 29842/57A GB 2984257 A GB2984257 A GB 2984257A GB 816168 A GB816168 A GB 816168A
Authority
GB
United Kingdom
Prior art keywords
methoxy
dimethylamino
carbon atoms
phenyl
formula
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
GB29842/57A
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.)
Boehringer Ingelheim Pharma GmbH and Co KG
Original Assignee
Dr Karl Thomae GmbH
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 Dr Karl Thomae GmbH filed Critical Dr Karl Thomae GmbH
Publication of GB816168A publication Critical patent/GB816168A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises compounds of the formula <FORM:0816168/IV (b)/1> and acid addition and quaternary salts thereof, wherein R1 and R2 are alkyl radicals or together with the nitrogen atom form a heterocyclic ring, optionally containing a further heteroatom, such as a piperidine morpholine or pyrrolidine ring, R3 is an alkyl group, R4 is an alkyl group of 1-5 carbon atoms or an alkoxy group, which must contain not less than 2 carbon atoms, when R3 is methyl, Z is a straight or branched alkylene radical of 1-4 carbon atoms and R5 is hydrogen or an alkyl or alkoxy group of 1-3 carbon atoms. The compounds are made by treating an amino-acetonitrile of the formula <FORM:0816168/IV (b)/2> with an organo-magnesium halide of the formula R5.C6H4.Z.Mg.Hal, preferably at an elevated temperature in a solvent or mixture of solvents chosen from ether, dibutyl ether, benzene and tetrahydrofuran, and if desired converting the products into quaternary salts or acid addition salts such as the hydrochloride, sulphate, phthalate or citrate. Preferred products include 1 - (3 - methyl - 4 - methoxy - phenyl)- and 1 - (3 - methoxy - 4 - propoxy - phenyl)-, 1 - dimethylamino - 3 - phenylpropane; 1 - (4-methoxy - 3 - methylphenyl) - 1 - dimethyl - amino-, 1 - (4 - methoxy - 3 - ethoxyphenyl)-1-diethylamino- and 1-(3 : 4-diethoxyphenyl)-1-dimethyl- and diethyl-amino-, 3-phenyl butane and 1 - (4 - ethoxy - 3 - methoxyphenyl) - 1 - dimethylamino-, 1 - (3 : 4 - diethoxyphenyl)-1-diethylamino-, 1 - (3 : 4 - diethoxyphenyl) - 1 - dimethylamino-, and 1-(4-methoxy-3-ethoxyphenyl) - 1 - dimethylamino-, 4 - phenyl butane. Many other products of the general formula given are specified.
GB29842/57A 1957-08-13 1957-09-23 Tertiary amines Expired GB816168A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH338468T 1957-08-13
DET12784A DE1087619B (en) 1957-08-13 1957-08-13 Process for the production of spasmolytic tertiary amines and their quaternary salts

Publications (1)

Publication Number Publication Date
GB816168A true GB816168A (en) 1959-07-08

Family

ID=25736828

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29842/57A Expired GB816168A (en) 1957-08-13 1957-09-23 Tertiary amines

Country Status (4)

Country Link
BE (1) BE560194A (en)
CH (1) CH344075A (en)
DE (1) DE1087619B (en)
GB (1) GB816168A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2503285A (en) * 1945-10-18 1950-04-11 Winthrop Stearns Inc Beta-substituted alpha, beta-diphenylethylamines and the preparation thereof

Also Published As

Publication number Publication date
BE560194A (en)
DE1087619B (en) 1960-08-25
CH344075A (en) 1960-01-31

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