Sertraline → Sertraline Hydrochloride

HRID 985737Notes

Reaction equation

HRID 985737 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-0b8b62cdd7f7464b99bc086125d2b1c3
Source dataset
uspto-grants-2005_03
Patent number
US06872853B1

Reaction notes

Loading…