Sertraline → Sertraline Hydrochloride

HRID 2118154Notes

Reaction equation

HRID 2118154 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>CC(C)=O>[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 180AcetoneSolvent

Conditions

Temperature
-5 °C

Procedure

50 g of sertraline free amine are dissolved in 500 ml acetone. This solution is clarified by filtration, and the clear solution is well stirred and heated to reflux temperature. At this temperature 2.5 g (5 mol %) of sertraline hydrochloride Form II are added after which directly the addition of the aqueous hydrogenchloride solution (32%) 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. temperatureheated
  3. temperatureto reflux temperature
  4. additionAt this temperature 2.5 g (5 mol %) of sertraline hydrochloride Form II are added after which directly
  5. additionthe addition of the aqueous hydrogenchloride solution (32%)

Sources & evidence

ORD record
ord-18f93b13a1a1492b805ab718791e07a3
Source dataset
uspto-grants-2008_10
Patent number
US07442838B2

Reaction notes

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