GB1045927A - 1-(2,4-dimethylphenyl)-2-pyrrolidinobutane and acid addition salts thereof - Google Patents

1-(2,4-dimethylphenyl)-2-pyrrolidinobutane and acid addition salts thereof

Info

Publication number
GB1045927A
GB1045927A GB27208/64A GB2720864A GB1045927A GB 1045927 A GB1045927 A GB 1045927A GB 27208/64 A GB27208/64 A GB 27208/64A GB 2720864 A GB2720864 A GB 2720864A GB 1045927 A GB1045927 A GB 1045927A
Authority
GB
United Kingdom
Prior art keywords
dimethylphenyl
reaction
pyrrolidine
butane
salt
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
GB27208/64A
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 GB1045927A publication Critical patent/GB1045927A/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
    • C07D295/027—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 containing only one hetero ring
    • C07D295/03—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 containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms

Landscapes

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

Abstract

The invention comprises the pyrrolidinobutane of the formula <FORM:1045927/C2/1> and acid addition salts thereof, and the preparation thereof by one of the following methods:-(a) reaction of a - pyrrolidino - n-butyronitrile with a 2,4-dimethyl-benzyl magnesium halide in an organic solvent, for example an ether solvent such as diethyl ether or tetrahydrofuran, followed by decomposition of the complex initially formed to yield the desired base or salt, or (b) reaction of a -pyrrolidino-b -(2,4 - dimethylphenyl) - propionitrile with an ethyl magnesium halide in an organic solvent such as an ether solvent, for example diethyl ether or tetrahydrofuran, followed by decomposition of the magnesium complex initially formed to yield the desired base or salt, or (c) addition of pyrrolidine to 1-(2,4-dimethylphenyl)-butene-(1) in the presence of a basic catalyst, preferably an alkali metal such as sodium or lithium, or (d) reductive amination of 1-(2,4-dimethylphenyl)-butanone-(2) with pyrrolidine, or (e) reaction of 1-(2,4-dimethylphenyl) 2-amino-butane with a 1,4-dihalogenobutane, e.g. dibromobutane, preferably in the presence of an acid-binding agent, such as an alkali metal acetate or carbonate, e.g. sodium acetate or sodium carbonate, or (f) reaction of a 1 - (2,4 - dimethylphenyl) - 2 - halogeno - butane, e.g. the 2-chloro compound, with pyrrolidine at elevated temperatures, preferably at a temperature above 100 DEG C., and preferably in a closed vessel. 1 - (2,4 - Dimethylphenyl) - 2 - chlorobutane is prepared from 1 - (2,4 - dimethylphenyl) - 2-hydroxybutane by heating with thionyl chloride. 1 - (2,4 - Dimethylphenyl) - butane - (2) is prepared by acidation of the corresponding alcohol. 1 - (2,4 - Dimethylphenyl) - 2 - aminobutane is prepared from the above ketone. Pharmaceutical compositions in conventional forms for oral or parental administration comprise the compound of the formula above or a salt thereof and an inert diluent or excipient. The said compositions have anorexigenic action and a pronounced activity in increasing the peripheral blood flow.
GB27208/64A 1963-07-12 1964-07-01 1-(2,4-dimethylphenyl)-2-pyrrolidinobutane and acid addition salts thereof Expired GB1045927A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DET24287A DE1265751B (en) 1963-07-12 1963-07-12 Process for the preparation of 1- (2,4-dimethylphenyl) -2-pyrrolidino-butane and its acid addition salts

Publications (1)

Publication Number Publication Date
GB1045927A true GB1045927A (en) 1966-10-19

Family

ID=7551384

Family Applications (1)

Application Number Title Priority Date Filing Date
GB27208/64A Expired GB1045927A (en) 1963-07-12 1964-07-01 1-(2,4-dimethylphenyl)-2-pyrrolidinobutane and acid addition salts thereof

Country Status (3)

Country Link
DE (1) DE1265751B (en)
FR (1) FR3582M (en)
GB (1) GB1045927A (en)

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1088962B (en) * 1956-04-26 1960-09-15 Thomae Gmbh Dr K Process for the preparation of N-substituted pyrrolidines, their salts and quaternary ammonium compounds
DE1093799B (en) * 1957-05-27 1960-12-01 Thomae Gmbh Dr K Process and production of N-substituted pyrrolidines, their salts and quaternary ammonium compounds

Also Published As

Publication number Publication date
FR3582M (en) 1965-10-04
DE1265751B (en) 1968-04-11

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