GB683950A - Improvements in and relating to the manufacture of amino carbinols and alkenes - Google Patents

Improvements in and relating to the manufacture of amino carbinols and alkenes

Info

Publication number
GB683950A
GB683950A GB1881549A GB1881549A GB683950A GB 683950 A GB683950 A GB 683950A GB 1881549 A GB1881549 A GB 1881549A GB 1881549 A GB1881549 A GB 1881549A GB 683950 A GB683950 A GB 683950A
Authority
GB
United Kingdom
Prior art keywords
diphenylhexanol
bromo
diphenylnonene
piperidino
diphenylhexene
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
GB1881549A
Inventor
Paul Anthony Barrett
Samuel Wilkinson
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 GB1881549A priority Critical patent/GB683950A/en
Publication of GB683950A publication Critical patent/GB683950A/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
    • C07D295/084—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 with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
    • C07D295/092—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 with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings with aromatic radicals attached to the chain

Abstract

The invention comprises aminocarbinols of the formula <FORM:0683950/IV (b)/1> and amino-alkenes of the formula <FORM:0683950/IV (b)/2> and their salts, except when made by the process of Specification 682,160; n is 3-8, R1 and R2 are the same or different alkyl groups of 1-4 carbon atoms or else complete a morpholine, pyrrolidine, piperidine or N-methylpiperazine ring. The compounds are made in each case by reacting the corresponding chlorine or bromine compounds with HNR1R2, preferably using two mols. of the latter. Examples describe the preparation of the following: 4-piperidino-1 : 1-diphenylbutanol, 5 - morpholino - 1 : 1 - diphenylpentanol, 5 - dibutylamino - 1 : 1 - diphenylpentanol, 5 - pyrrolidino - 1 : 1 - diphenyl - pentanol, 6 - piperidino - 1 : 1 - diphenylhexanol, 6 - pyrrolidino - 1 : 1 - diphenylhexanol, 6 - morpholino - 1 : 1 - diphenylhexanol, 6 - dimethylamino - 1 : 1 - diphenylhexanol, 6 - diethylamino - 1 : 1 - diphenylhexanol, 6 - dibutylamino - 1 : 1 - diphenylhexanol, 6-(41-methylpiperazino)-1 : 1-diphenylhexanol, 9-piperidino-1 : 1-diphenylnonanol, 4-diethylamino - 1 : 1 - diphenylbutene, 5 - morpholino - 1 : 1 - diphenylpentene, 5 - pyrrolidino-1 : 1 - diphenylpentene, 6 - piperidino - 1 : 1 - diphenylhexene, 6 - dimethylamino - 1 : 1 - diphenylhexene, 6-(41-methylpiperazino)-1 : 1-diphenylhexene, 9 - piperidino - 1 : 1 - diphenylnonene, 9 - dibutylamino - 1 : 1 - diphenylnonene, 9 - morpholino - 1 : 1 - diphenylnonene and 9 - pyrrolidino - 1 : 1 - diphenylnonene. Salts described are hydrochlorides and oxalates. A further method of preparing the aminocarbinols is described in Specification 682,161. The starting materials are made by reacting chloro- or bromo-esters Hal-(CH2)nCOOR with a phenylmagnesium halide or phenyllithium to give (C6H5)2C(OH)-(CH2)n-Hal, and if desired dehydrating the latter to the alkenes (C6H5)2C : CH(CH2)n-1-Hal by distillation alone or with a mineral acid. Examples are given of the preparation of the following: 4 - chloro - 1 : 1 - diphenylbutanol, 5 - bromo - 1 : 1 - diphenylpentanol, 6 - bromo - 1 : 1 -diphenylhexanol, 9 - bromo - 1 : 1 - diphenylnonanol, 4 - chloro - 1 : 1 - diphenylbutene, 5 - bromo - 1 : 1 - diphenylpentene, 6 - bromo - 1 : 1-diphenylhexene and 9-bromo-1 : 1-diphenylnonene. According to the Provisional Specification n may be up to 11, the phenyl groups may be substituted and if NR3R4 is a heterocyclic ring it may carry alkyl substituents. It is also stated that the halocarbinols may be dehydrated by heating with carboxylic acid chlorides or anhydrides.
GB1881549A 1949-07-18 1949-07-18 Improvements in and relating to the manufacture of amino carbinols and alkenes Expired GB683950A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1881549A GB683950A (en) 1949-07-18 1949-07-18 Improvements in and relating to the manufacture of amino carbinols and alkenes

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1881549A GB683950A (en) 1949-07-18 1949-07-18 Improvements in and relating to the manufacture of amino carbinols and alkenes

Publications (1)

Publication Number Publication Date
GB683950A true GB683950A (en) 1952-12-10

Family

ID=10118887

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1881549A Expired GB683950A (en) 1949-07-18 1949-07-18 Improvements in and relating to the manufacture of amino carbinols and alkenes

Country Status (1)

Country Link
GB (1) GB683950A (en)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2826590A (en) * 1954-03-22 1958-03-11 Lilly Co Eli Synthesis of tricyclamol
US2881172A (en) * 1956-09-10 1959-04-07 Abbott Lab Chemical compounds
US2907766A (en) * 1956-09-10 1959-10-06 Abbott Lab Piperazine derivatives
US2925420A (en) * 1957-09-25 1960-02-16 Abbott Lab Piperazine derivatives
US2989533A (en) * 1957-07-18 1961-06-20 Hoechst Ag Basically substituted diphenyl-carbinol esters and a process for preparing them
US3088869A (en) * 1961-08-29 1963-05-07 Smith Kline French Lab Antiemetic compositions and methods of treating nausea and vomiting

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2826590A (en) * 1954-03-22 1958-03-11 Lilly Co Eli Synthesis of tricyclamol
US2881172A (en) * 1956-09-10 1959-04-07 Abbott Lab Chemical compounds
US2907766A (en) * 1956-09-10 1959-10-06 Abbott Lab Piperazine derivatives
US2989533A (en) * 1957-07-18 1961-06-20 Hoechst Ag Basically substituted diphenyl-carbinol esters and a process for preparing them
US2925420A (en) * 1957-09-25 1960-02-16 Abbott Lab Piperazine derivatives
US3088869A (en) * 1961-08-29 1963-05-07 Smith Kline French Lab Antiemetic compositions and methods of treating nausea and vomiting

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