GB657302A - Improvements in and relating to the preparation of substituted aralkanolamine and derivatives thereof - Google Patents

Improvements in and relating to the preparation of substituted aralkanolamine and derivatives thereof

Info

Publication number
GB657302A
GB657302A GB593248A GB593248A GB657302A GB 657302 A GB657302 A GB 657302A GB 593248 A GB593248 A GB 593248A GB 593248 A GB593248 A GB 593248A GB 657302 A GB657302 A GB 657302A
Authority
GB
United Kingdom
Prior art keywords
piperidino
phenyl
hydrochloride
alkyl
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
GB593248A
Inventor
Donald Wallace Adamson
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.)
Wellcome Foundation Ltd
Original Assignee
Wellcome Foundation 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 Wellcome Foundation Ltd filed Critical Wellcome Foundation Ltd
Priority to GB593248A priority Critical patent/GB657302A/en
Publication of GB657302A publication Critical patent/GB657302A/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
    • C07D295/04—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)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)

Abstract

Amines of the formula <FORM:0657302/IV (b)/1> (in which R1 is an aryl group which may be substituted by alkyl or alkoxy groups, R2 and R3 are hydrogen atoms or an alkyl radical, R4 is hydrogen, R5 is hydrogen or an alkyl radical and R6 and R7 may be the same or different alkyl, alkenyl or aralkyl groups or -NR6R7 may be a pyrrolidino-, morpholino- or piperidino group) are prepared by treating with one another the corresponding b -aminoethyl aryl ketone or a salt thereof and the appropriate alkyl magnesium halide or organo-lithium compound and hydrolysing the organometallic compound produced. The reaction is preferably carried out in an anhydrous mutual solvent by allowing to stand or by heating until reaction is complete. The product is hydrolysed, suitably by addition of water followed by acetic acid, to give a salt of the base, which, if insoluble, may be separated by filtration and converted to the free base by treating with aqueous alkali, or if soluble in the reaction mixture, is basified with aqueous alkali, and extracted with an organic solvent which is subsequently evaporated. The 3-aryl-3-hydroxy alkyl tertiary amines formed may be converted into the corresponding quaternary salts by treatment with an alkyl or aralkyl halide. The quaternization may be effected in a solvent such as acetone, methanol, ethanol or dioxane. In examples the following compounds are prepared in each case by means of the Grignard reaction: (1) 1-N-piperidino-3-phenyl - nonan - 3 - ol; (2) 1 - dimethylamino - 3 - phenyl - butan - 3 - ol; (3) 1 - N - piperidino-3 - phenyl - 4 - methyl - pentan - 3 - ol; (4) 1 - N - piperidino - 3 - phenyl - heptan - 3 - ol and its salt with methyl iodide; (5) 1-N-piperidino-3-phenyl-pentan-3-ol, and its hydrochloride; (6) 1 - N - piperidino - 3 - phenyl - hexan - 3 - ol, and its hydrochloride; (7) 1-N-piperidino-3-phenyl-octan-3-ol, and its hydrochloride; (8) 1 - N - piperidino - 3 - phenyl - decan - 3 - ol, and its hydrochloride; (9) 1-N-piperidino-3-phenylundecan-3-ol, and its hydrochloride; (10) 1-diethylamino - 3 - phenyl - octan - 3 - ol, and its hydrochloride; (11) 1-dibutylamino-3-phenylhexan-3-ol, and its hydrochloride; (12) 1-N-piperidino-3-p-tolyl-hexan-3-ol, and its hydrochloride. Specification 307,304, [Class 2 (iii)], is referred to.
GB593248A 1948-02-27 1948-02-27 Improvements in and relating to the preparation of substituted aralkanolamine and derivatives thereof Expired GB657302A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB593248A GB657302A (en) 1948-02-27 1948-02-27 Improvements in and relating to the preparation of substituted aralkanolamine and derivatives thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB593248A GB657302A (en) 1948-02-27 1948-02-27 Improvements in and relating to the preparation of substituted aralkanolamine and derivatives thereof

Publications (1)

Publication Number Publication Date
GB657302A true GB657302A (en) 1951-09-19

Family

ID=9805323

Family Applications (1)

Application Number Title Priority Date Filing Date
GB593248A Expired GB657302A (en) 1948-02-27 1948-02-27 Improvements in and relating to the preparation of substituted aralkanolamine and derivatives thereof

Country Status (1)

Country Link
GB (1) GB657302A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2765307A (en) * 1953-02-11 1956-10-02 Rohm & Haas Hydroxyamines
US2854483A (en) * 1954-10-06 1958-09-30 American Home Prod Bronchodilator compounds

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2765307A (en) * 1953-02-11 1956-10-02 Rohm & Haas Hydroxyamines
US2854483A (en) * 1954-10-06 1958-09-30 American Home Prod Bronchodilator compounds

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