Sodium Hydroxide → HCID 131723760, compound

Participants

Reaction Conditions

Reaction Steps

Sertraline mandelate (750 grams) was slurried in a mixture of water (3.9 L) and ethyl acetate (3.9 L). The slurry was cooled to 15° C. NaOH (25% aqueous, 250 mL) was added, resulting in a solution with pH 9.6. The free base of sertraline was partitioned into the ethyl acetate layer which was separated. The aqueous layer was extracted with an additional 3.4 liters of ethyl acetate. The combined ethyl acetate layers were washed with 3.9 liters of water. The ethyl acetate layer containing sertraline base was concentrated under vacuum and filtered to clarify the solution. To this solution was added L-lactic acid (155 g). The reaction mixture was granulated hr 20 hours at room temperature. The solids were filtered, washed 4 times with ethyl acetate(400 mL each time). The crystals were dried overnight under vacuum at 40° C. The yield was calculated to be 84%. mp 153° C.

Provenance & Evidence