Sertraline → HCID 131723760, compound

HRID 1058525Notes

Reaction equation

[CH3:1][NH:2][C@@H:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:20])=[C:17]([Cl:19])[CH:18]=2)[CH2:5][CH2:4]1.[C:21]([OH:26])(=[O:25])[C@H:22]([CH3:24])[OH:23]>C(OCC)(=O)C>[CH3:1][NH:2][C@@H:3]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[C@H:6]([C:13]2[CH:14]=[CH:15][C:16]([Cl:20])=[C:17]([Cl:19])[CH:18]=2)[CH2:5][CH2:4]1.[C:21]([O-:26])(=[O:25])[C@H:22]([CH3:24])[OH:23]

Participants

Conditions

Temperature: 40 °C

Procedure

Sertraline base (the compound of Preparation AA, 1.0 g) was dissolved in ethyl acetate (20 mL) in a 50 mL round bottom flask and the solution was heated to 40° C. L-Lactic acid (342.5 mg) was separately dissolved in ethyl acetate (5 mL). The L-latic acid solution was added in small portions to the solution in the round bottom flask which was constantly stirred with a magnetic stirred. The reaction mixture was stirred at 40° C. for 2 hours after the addition of the L-lactic acid solution was complete. The reaction mixture was then allowed to cool to room temperature and the solids were filtered. The solids were washed with 5 mL of ethyl acetate and then dried under vacuum at 40° C. for 24 hours. The dried solid was identified as the L-lactate salt of sertraline. The yield was calculated to be 86%. mp 153° C.

Workup

additionThe L-latic acid solution was added in small portions to the solution in the round bottom flask which
stirringThe reaction mixture was stirred at 40° C. for 2 hours
temperatureto cool to room temperature
filtrationthe solids were filtered
washThe solids were washed with 5 mL of ethyl acetate
customdried under vacuum at 40° C. for 24 hours

Sources & evidence

ORD record: ord-adeecfb82899433c9d568cf3b8729f62
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06517866B1

Reaction notes

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