Sertraline → Sertraline Hydrochloride

HRID 853173Notes

Reaction equation

HRID 853173 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].CC(N(C)C)=O>C(#N)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:21]

Participants

4

Reactant 2

HCID 68617SertralineHCID 523006HCID 523006, compound

Product 1

HCID 63009Sertraline HydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

30 g sertraline base is dissolved in 450 ml acetonitrile at room temperature. To this solution a solution of 13.3 g dimethylacetamide hydrochloride in 150 ml acetonitrile is added under stirring within 15 minutes. While adding solution of dimethylacetamide hydrochloride sertraline hydrochloride precipitates nicely in the crystalline Form II. After stirring the suspension for another hour, the product is filtered off, washed twice with 50 ml acetone and dried at 50° C. under vacuum for three hours to yield 31.3 g (94%) of sertraline hydrochloride form II.

Workup

  1. customprecipitates nicely in the crystalline Form II
  2. stirringAfter stirring the suspension for another hour
  3. filtrationthe product is filtered off
  4. washwashed twice with 50 ml acetone
  5. customdried at 50° C. under vacuum for three hours

Sources & evidence

ORD record
ord-9a6c1a460e114664a1393c407d4aba34
Source dataset
uspto-grants-2007_08
Patent number
US07253320B2

Reaction notes

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