Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpi

Details Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpi Process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpi

1980-12-04

1983-03-22

Milestone, Norma S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

546240, 546340, C07D21114

Patent

active

043776914

ABSTRACT:
A process for the preparation of 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol (i.e. ifenprodil) and acid-addition salts thereof, characterized by brominating 4'-hydroxypropiophenone in a single or mixed solvent selected from the group consisting of methanol, ethanol and a saturated aliphatic ether, removing hydrogen bromide formed in the course of the bromination, adding 4-benzylpyridine to the reaction mixture, heating the reaction mixture under reflux in a single or mixed solvent selected from the group consisting of methanol and ethanol, and then subjecting the resultant reaction mixture to catalytic reduction to form 1-(4-hydroxyphenyl)-2-(4-benzylpiperidino)-1-propanol hydrobromide in the reaction mixture. The end product (i.e. ifenprodil) can be obtained according to this process in a high yield of about 80% within 14 hours from the starting material in a single reaction container throughout the process, without introducing a protective benzyl group into the starting material prior to the bromination.

REFERENCES:
patent: 2695919 (1954-11-01), Wright et al.
patent: 3509164 (1970-04-01), Carron et al.
Chemische Berichte, vol. 86, No. 12, (1953), pp. 1556-1558.
A. V. Dombrovskii et al., Jour. Gen. Chem. USSR, vol. 32, (1962), pp. 2246-2248.
S. J. Pasaribu et al., Aus. J. Chem., vol. 26, (1973), pp. 1327-1331.
Alan E. Ardis et al., Jour. Am. Chem. Soc., vol. 68, (1946), pp. 591-595.

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