Sertraline → Sertraline Hydrochloride

HRID 1281239Notes

Reaction equation

HRID 1281239 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>CO.CCCCCC>[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

4

Reactant 1

HCID 68617Sertraline

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8058HexaneSolvent

Conditions

Temperature
30 °C

Procedure

Sertraline base (10 g) was dissolved in a mixture of methanol (100 mL) and hexane (100 mL). Gaseous HCI was bubbled through the mixture at 35° C. until a pH of 1 was reached, at which point the mixture had clarified. The resulting solution was stirred at 30° C. for two hours over which time crystals formed. The crystals were filtered and were identified as sertraline hydrochloride Form XIV by their powder X-ray spectrum that exhibited reflections at 7.4±0.2, 9.6±0.2, 12.0±0.2, 12.8±0.2, 14.3±0.2, 16.0±0.2, 16.2±0.2, 18.0±0.2, 21.1±0.2, 23.2±0.2, 23.6±0.2, 24.3±0.2, 24.9±0.2, 25.7±0.2, 26.7±0.2, 29.6±0.2 and 32.5±0.2 degrees two-theta.

Workup

  1. customGaseous HCI was bubbled through the mixture at 35° C. until a pH of 1
  2. customformed
  3. filtrationThe crystals were filtered
  4. customwere identified as sertraline hydrochloride Form XIV by their powder X-ray spectrum that exhibited reflections at 7.4±0.2, 9.6±0.2, 12.0±0.2, 12.8±0.2, 14.3±0.2, 16.0±0.2, 16.2±0.2, 18.0±0.2, 21.1±0.2, 23.2±0.2, 23.6±0.2, 24.3±0.2, 24.9±0.2, 25.7±0.2, 26.7±0.2, 29.6±0.2 and 32.5±0.2 degrees two-theta

Sources & evidence

ORD record
ord-8273ba00d2424286b8abbd0762f01ec7
Source dataset
uspto-grants-2002_09
Patent number
US06452054B2

Reaction notes

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