“A Process For The Preparation Of Ormeloxifene (I) And Its Pharmaceutically Acceptable Salt Ormeloxifene Hydrochloride”

Abstract: The present invention relates to a simple process for the preparation of Ormeloxifene (I), a non-hormonal oral contraceptive and its derivatives. The process as shown in FIG. 2 comprises the steps of: Perkin reaction between 4-hydroxybenzaldehyde (II) and phenylacetic acid (III) to give 3-(4-acetoxyphenyl)-2-phenylacrylic acid (IV). The obtained intermediate 3-(4-acetoxyphenyl)-2-phenylacrylic acid (IV) is hydroarylated with 3- methoxyphenol (V) to produce 4-(4-hydroxyphenyl)-7-methoxy-3-phenylchroman-2-one (VI). Then, the Grignard reagent is used to convert 4-(4-hydroxyphenyl)-7-methoxy-3- phenylchroman-2-one (VI) to 7-methoxy-2,2-dimethyl-3-phenylchroman-4-yl) phenol (VII). Ormeloxifene (I)is produced by the nucleophilic substitution between 7-methoxy-2,2- dimethyl-3-phenylchroman-4-yl) phenol (VII) and 1-(2-chloroethyl) pyrrolidine hydrochloride (VIII). On other hand, Ormeloxifene (I) (2,2-dimethyl-3-phenyl-4-{4-(2- pyrrolidinoethyl) phenyl}-7-methoxychroman) is reacted with hydrochloric acid to produce pharmaceutically acceptable salt Ormeloxifene hydrochloride (IX). Thus, the present invention provides an economic and eco-friendly process adaptable for large scale manufacture with better yield.

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