Sertraline → Sertraline Hydrochloride

HRID 985738Notes

Reaction equation

HRID 985738 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(C(C)=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.[ClH:19]

Participants

3

Reactant 1

HCID 68617Sertraline

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

10 g sertraline free amine are dissolved in 85 ml methyl ethyl ketone. This solution is clarified by filtration, and the clear solution is well stirred and heated to 60° C. At this temperature 0.5 g (5 mol %) of sertraline hydrochloride Form II are added after which directly the addition of the aqueous hydrogenchloride solution (37%) is started until pH<5. The resulting white suspension is cooled to −5° C. and sertraline hydrochloride is isolated by filtration and dried in vacuum. The sertraline Is obtained as Form II.

Workup

  1. filtrationThis solution is clarified by filtration
  2. additionAt this temperature 0.5 g (5 mol %) of sertraline hydrochloride Form II are added after which directly
  3. additionthe addition of the aqueous hydrogenchloride solution (37%)
  4. temperatureThe resulting white suspension is cooled to −5° C.

Sources & evidence

ORD record
ord-e94468e8ca5b4d6881689e23dc77def4
Source dataset
uspto-grants-2005_03
Patent number
US06872853B1

Reaction notes

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