Hydrochloric Acid → Sertraline Hydrochloride

HRID 2301701Notes

Reaction equation

HRID 2301701 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.CO.C(O)C.[ClH:26]>O.C(OCC)(=O)C.C(O)(C)C.CCCCCC>[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.[ClH:26]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 887MethanolHCID 68617Sertraline

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Alternatively, sertraline base is added to a solvent selected from the group consisting of methanol, ethanol, water, hexane, isopropyl alcohol, and ethyl acetate or a mixture thereof. The solution is heated and concentrated hydrochloric acid is added. Water may also be added. Sertraline hydrochloride Form V is isolated by allowing the mixture to cool to room temperature and remain at room temperature overnight, followed by filtration and drying.

Workup

  1. temperatureThe solution is heated

Sources & evidence

ORD record
ord-a1f30d048dab400680fb3365039490e8
Source dataset
uspto-grants-2002_12
Patent number
US06500987B1

Reaction notes

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