Toluene → HCID 12986614, compound

Participants

Reaction Conditions

Reaction Steps

The toluene solution containing citalopram base was mixed with 1,2-dichloromethane (400 lit) and cooled to 10-15° C. A solution of 1-chloro ethyl chloroformate (110.8 Kg, 0.77 kmoles) was added to the reaction mass below 20° C. The reaction mass was further stirred for 30 minutes at 15-20° C. Diisopropylethyl amine (30.24 Kg, 0.23 kmoles) was added to the reaction mixture below 20° C. and further stirred for 30 minutes. The temperature of the reaction mass was raised to 60-65° C. and maintained for 2-3 hrs. The reaction mass was diluted with methanol (320 lit) at 60-65° C., heated further for 2-4 hrs at 60-65° C. and evaporated. The reaction mass was cooled to 25-30° C., diluted with water (480 lit) and stirred for 30 minutes. The phases were separated, aqueous layer was extracted with toluene (2×200 lit) and pH of the aqueous layer was adjusted to 9-10 with ammonia solution (320 lit). Toluene (400 lit) was added and the reaction mass stirred for 30 minutes. The organic layer was separated. Aqueous layer was extracted with toluene (2×200 lit). The combined toluene layer was washed with water, followed by brine. The toluene layer was dried on sodium sulphate, filtered and stirred with charcoal (15 Kg). The reaction mass was filtered and evaporated under reduced pressure to afford the title compound. Yield—140 Kg, 91.5%

Provenance & Evidence