Sertraline → Sertraline Hydrochloride

HRID 853174Notes

Reaction equation

HRID 853174 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].CN1CCCC1=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 186298211-Methylpyrrolidin-2-one--hydrogen chloride (1/1)

Product 1

HCID 63009Sertraline HydrochlorideYield 95.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

20 g sertraline base is dissolved in 300 ml acetonitrile at room temperature. To this solution a solution of 9.75 g N-methylpyrrolidin-2-on hydrochloride in 100 ml acetonitrile is added under stirring within 15 minutes. After stirring for 45 minutes, the crystals are filtered off, washed twice with 40 ml acetone and dried at 50° C. under vacuum for three hours to yield 21.28 g (95%) of sertraline hydrochloride form II.

Workup

  1. stirringAfter stirring for 45 minutes
  2. filtrationthe crystals are filtered off
  3. washwashed twice with 40 ml acetone
  4. customdried at 50° C. under vacuum for three hours

Sources & evidence

ORD record
ord-38be23fb2c9848b7b4ee47d461d932f6
Source dataset
uspto-grants-2007_08
Patent number
US07253320B2

Reaction notes

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