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GB1153436A - Optically Active Benzhydrol Derivatives and Processes for the Preparation thereof - Google Patents

Optically Active Benzhydrol Derivatives and Processes for the Preparation thereof

Info

Publication number
GB1153436A
GB1153436A GB31226/66A GB3122666A GB1153436A GB 1153436 A GB1153436 A GB 1153436A GB 31226/66 A GB31226/66 A GB 31226/66A GB 3122666 A GB3122666 A GB 3122666A GB 1153436 A GB1153436 A GB 1153436A
Authority
GB
United Kingdom
Prior art keywords
dextro
carbinol
ester
isomer
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
GB31226/66A
Inventor
Jules Jarrousse
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.)
YAB SOC
Original Assignee
YAB SOC
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 YAB SOC filed Critical YAB SOC
Priority to GB31226/66A priority Critical patent/GB1153436A/en
Publication of GB1153436A publication Critical patent/GB1153436A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/10—Separation; Purification; Stabilisation; Use of additives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
    • C07C213/02—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions involving the formation of amino groups from compounds containing hydroxy groups or etherified or esterified hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B2200/00—Indexing scheme relating to specific properties of organic compounds
    • C07B2200/07—Optical isomers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

1,153,436. Benzhydrol derivatives. SOC. YAB. 12 July, 1966, No. 31226/66. Heading C2C. Optical isomers of carbinols of the formula R 1 -C 6 H 4 -CH(OH)-C 6 H 4 -R 2 (wherein R 1 is alkyl, alkoxy or halogen, and R 2 is H, alkyl, alkoxy or halogen, and if R 1 and R 2 are the same then they occupy different positions in the respective benzene nuclei) are prepared by forming a racemic hemi-ester of the carbinol with a dibasic acid, reacting the ester with an optically active alkaloid to form a mixture of diastereoisomeric salts, treating this mixture with a suitable solvent e.g. a lower alkanol such as ethanol, from which a crystallized fraction containing the salt of the laevo ester is obtained, treating the mother liquor with aqueous sodium hydroxide to obtain the crude dextro isomer of the carbinol therefrom, and purifying this by crystallization from a petroleum hydrocarbon to obtain the pure dextro isomer. Preferred reactants are p-tolylphenylcarbinol, phthalic or succinic acid and l-quinine. The laevo isomer of the carbinol obtained from the alkaloid salt of its hemi-ester with a dibasic acid may be racemized by treatment with a dilute acid and resolved again to obtain further quantities of the dextro isomer, which may then be reacted with a chlorinated aliphatic tertiary amine, the chlorine atom of which is bound to a primary or secondary carbon atom, in the presence of an aqueous solution of potassium or sodium hydroxide, to obtain an amino ether of the dextro carbinol, which may be isolated and purified as the free base or a salt thereof. The chlorinated amine preferably has the formula Cl.C n H 2n .N(A.B) wherein n is 1 to 5 and A and B are alkyl radicals. The amino-ethers of the dextro carbinols referred to above are stated to have antihistaminic activity and may be made up into pharmaceutical compositions such as syrups, tablets and suppositories. The specific compound d - 4<SP>1</SP> - methyldiphenyl - (dimethylaminoethoxy) - methane is also stated to possess a spasmolytic anti-acetylcholine action and slight mydriatic, hypotensive, vasodilative, local anaesthetic and soporific activities.
GB31226/66A 1966-07-12 1966-07-12 Optically Active Benzhydrol Derivatives and Processes for the Preparation thereof Expired GB1153436A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB31226/66A GB1153436A (en) 1966-07-12 1966-07-12 Optically Active Benzhydrol Derivatives and Processes for the Preparation thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB31226/66A GB1153436A (en) 1966-07-12 1966-07-12 Optically Active Benzhydrol Derivatives and Processes for the Preparation thereof

Publications (1)

Publication Number Publication Date
GB1153436A true GB1153436A (en) 1969-05-29

Family

ID=10319929

Family Applications (1)

Application Number Title Priority Date Filing Date
GB31226/66A Expired GB1153436A (en) 1966-07-12 1966-07-12 Optically Active Benzhydrol Derivatives and Processes for the Preparation thereof

Country Status (1)

Country Link
GB (1) GB1153436A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0214572A2 (en) * 1985-08-30 1987-03-18 Stauffer Chemical Company Racemization of optically active compounds having a chlorine substituted chiral carbon atom
EP0216196A2 (en) * 1985-08-30 1987-04-01 Stauffer Chemical Company Racemization of optically active compounds having a bromine substituted chiral carbon atom
EP0385491A1 (en) * 1989-03-03 1990-09-05 MAGIS FARMACEUTICI S.p.A. Optically active isomer of cloperastine possessing antitussive activity, a process for its preparation and pharmaceutical compositions which contain it

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0214572A2 (en) * 1985-08-30 1987-03-18 Stauffer Chemical Company Racemization of optically active compounds having a chlorine substituted chiral carbon atom
EP0216196A2 (en) * 1985-08-30 1987-04-01 Stauffer Chemical Company Racemization of optically active compounds having a bromine substituted chiral carbon atom
EP0216196A3 (en) * 1985-08-30 1988-09-21 Stauffer Chemical Company Racemization of optically active compounds having a bromine substituted chiral carbon atom
EP0214572A3 (en) * 1985-08-30 1988-09-28 Stauffer Chemical Company Racemization of optically active compounds having a chlorine substituted chiral carbon atom
EP0385491A1 (en) * 1989-03-03 1990-09-05 MAGIS FARMACEUTICI S.p.A. Optically active isomer of cloperastine possessing antitussive activity, a process for its preparation and pharmaceutical compositions which contain it

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Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PLNP Patent lapsed through nonpayment of renewal fees