Hydrochloric Acid → Sertraline Hydrochloride

HRID 1359614Notes

Reaction equation

HRID 1359614 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]>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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68617Sertraline

Product 1

HCID 63009Sertraline HydrochlorideYield 76.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

Sertraline base (2.7 g) was suspended in 27 mL of water. This mixture was heated to 80° C. and treated with hydrochloric acid until about pH 1 was reached. A clear solution was obtained, which on cooling gave a precipitate. After 2 hours stirring at room temperature the solid was isolated by filtration. This solid was characterized by powder x-ray diffraction (see FIG. 3, Form VIII). Drying for 24 hours at ˜50° C. yielded 2.32 g (76.8%) of sertraline hydrochloride Form IX, characterized by powder x-ray diffraction, infra-red absorption, differential scanning calorimetry, and thermal gravimetric analysis as set forth above and depicted in FIGS. 8, 10, and 12.

Workup

  1. customA clear solution was obtained
  2. temperaturewhich on cooling
  3. customgave a precipitate
  4. customwas isolated by filtration
  5. customDrying for 24 hours at ˜50° C.

Sources & evidence

ORD record
ord-ac1b3367248a4dcbbec2ea6724564b4f
Source dataset
uspto-grants-2003_07
Patent number
US06600073B1

Reaction notes

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