Norchlorcyclizine → 4-[4-(4-Chlorobenzhydryl)piperazino]methyl-2-dimethylaminophenol

Participants

Reaction Steps

To a solution of 3-dimethylamino-4-hydroxybenzaldehyde (see Synthesis of Compound A) (600 mg, 3.63 mmol) in methanol (10 ml) was added 1-(4-chlorobenzhydryl)piperazine (1.25 g, 4.36 mmol) while stirring at room temperature. Thereto was added sodium cianoborohydride (95% content) (700 mg, 10.6 mmol) by portions. After stirring for 1 hour, acetic acid (0.2 ml) was added thereto, and the mixture was further stirred for 3 hours. The reaction mixture was poured into water, and the pH of the solution was made basic by the addition of a saturated aqueous solution of sodium hydrogencarbonate. The solution was extracted with ethyl acetate and washed with a saturated aqueous solution of sodium hydrogencarbonate. The extract was then extracted with 1N hydrochloric acid, and the aqueous layer was neutralized and extracted with ethyl acetate. Then thus obtained extract was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel to give the object Compound 7. Yield 569 mg (36%).

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