Sertraline → Sertraline Hydrochloride

HRID 2118156Notes

Reaction equation

HRID 2118156 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(C)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 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
60 °C

Procedure

40 g sertraline free amine are dissolved in 360 ml methyl isobutyl ketone. This solution is clarified by filtration, and the clear solution is well stirred and heated to 60° C. At this temperature 2 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 20° 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 2 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 20° C.

Sources & evidence

ORD record
ord-ab0a81ab352c4a359abd80cf92902f84
Source dataset
uspto-grants-2008_10
Patent number
US07442838B2

Reaction notes

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