Ammonia → Sertraline Hydrochloride

HRID 458231Notes

Reaction equation

HRID 458231 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.[Cl-:21].[NH4+].N>C(OCC)(=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 3

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 90.6%

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Procedure

In a solution of sertraline base (50 g) in ethyl acetate/water 10/1 (400 ml), ammonium chloride (8,7 g) was added. The resulting mixture was heated at reflux temperature and stirred for 15 hours during which ammonia evolution was observed and a white crystalline solid precipitated. When the evolution of ammonia ended the solid product was filtered, washed with ethyl acetate and dried under vacuum. 50,5 g of sertraline hydrochloride form I (yield 90%) were obtained.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux temperature
  3. customa white crystalline solid precipitated
  4. filtrationwas filtered
  5. washwashed with ethyl acetate
  6. customdried under vacuum

Sources & evidence

ORD record
ord-41c32483a4294f719f342d44bf0a8e16
Source dataset
uspto-grants-2007_03
Patent number
US07189876B2

Reaction notes

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