Sertraline → Sertraline Hydrochloride

HRID 458233Notes

Reaction equation

HRID 458233 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.[ClH:21].N1C=CC=CC=1>CC(O)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:21]

Participants

5

Reactant 2

HCID 68617SertralineHCID 10176127Pyridinium chloride

Product 1

HCID 63009Sertraline HydrochlorideYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of sertraline base (50 g) in propan-2-ol (200 ml) was diluted with water (50 ml) and pyridine hydrochloride (18,9 g) was added at room temperature under nitrogen. The reaction mixture was stirred at room temperature for 1 hour and the solid that crystallised was isolated by filtration, washed with propan-2-ol and dried under vacuum. 49,2 g of sertraline hydrochloride form V (yield 88%) were obtained.

Workup

  1. additionwas added at room temperature under nitrogen
  2. customthe solid that crystallised
  3. customwas isolated by filtration
  4. washwashed with propan-2-ol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-9bb385902a044a38933d45820361db2c
Source dataset
uspto-grants-2007_03
Patent number
US07189876B2

Reaction notes

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