Sertraline → HCID 131723760, compound

HRID 1058524Notes

Reaction equation

HRID 1058524 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

4

Reactant 2

HCID 68617Sertraline3×HCID 107689L-Lactic Acid3×

Product 1

HCID 131723760HCID 131723760, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sertraline base (the compound of Preparation AA, 200 mg) was dissolved in ethyl acetate (200 μL) in a 10 mL conical reaction vial. L-Lactic acid (solid, 68.5 mg) was separately dissolved in ethyl acetate(100 μL). The L-lactic acid solution was added to the sertraline base solution under constant stirring with a magnetic stirrer. A precipitate was observed within about 2 minutes after complete addition of the L-lactic acid solution to the sertraline base solution. The reaction mixture was allowed to granulate overnight (18 hour) at room temperature. The precipitate was filtered and the solid was rinsed with 1 mL of ethyl acetate. The solid was dried in a vacuum oven at 40° C. for 20 hours. The dried sold was characterized and identified as the L-lactate salt of sertraline. The yield was determined to be 72%. mp 153° C.

Workup

  1. waitto granulate overnight
  2. custom(18 hour)
  3. customat room temperature
  4. filtrationThe precipitate was filtered
  5. washthe solid was rinsed with 1 mL of ethyl acetate
  6. customThe solid was dried in a vacuum oven at 40° C. for 20 hours

Sources & evidence

ORD record
ord-865077d686684f54a00f2a68fbc3d486
Source dataset
uspto-grants-2003_02
Patent number
US06517866B1

Reaction notes

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