Sertraline → HCID 131723760, compound

HRID 1058526Notes

Reaction equation

HRID 1058526 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(O)(C)C.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

5

Reactant 2

HCID 68617SertralineHCID 107689L-Lactic Acid3×

Product 1

HCID 131723760HCID 131723760, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

Sertraline base (10 g)was dissolved in isopropanol (150 mL) in a 500 mL round bottom flask and the solution was heated to 40° C. L-Lactic acid (3.4 g) was separately dissolved in ethyl acetate (25 mL). The L-lactic acid solution was added in small portions to the solution in the round bottom flask which was constantly stirred with a magnetic stirrer. The reaction mixture was stirred at 40° C. for 4 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 50 mL of hexane and then dried under vacuum at 40° C. for 48 hours. The dried solid was identified as the L-lactate salt of sertraline. The yield was calculated to be 94%. mp 153° C.

Workup

  1. stirringThe reaction mixture was stirred at 40° C. for 4 hours
  2. temperatureto cool to room temperature
  3. filtrationthe solids were filtered
  4. washThe solids were washed with 50 mL of hexane
  5. customdried under vacuum at 40° C. for 48 hours

Sources & evidence

ORD record
ord-d0e9a83cfa474054b8e40a4614c12650
Source dataset
uspto-grants-2003_02
Patent number
US06517866B1

Reaction notes

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