Hydrochloric Acid → Sertraline Hydrochloride

HRID 1359609Notes

Reaction equation

HRID 1359609 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 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

Sertraline base (3 g) was stirred with 35 mL water. The slurry was heated at ˜70° C. and, while maintaining this temperature, concentrated hydrochloric acid was added until pH 1 was reached. During acidification, almost complete dissolution was observed followed by precipitation. The mixture was cooled to room temperature and stirred for 2 hours. The solid was isolated by filtration, washed with water and dried overnight at 50-60° C., yielding 3.23 g (96%) sertraline hydrochloride Form V.

Workup

  1. additionwas added until pH 1
  2. dissolutionDuring acidification, almost complete dissolution
  3. customwas observed followed by precipitation
  4. temperatureThe mixture was cooled to room temperature
  5. customThe solid was isolated by filtration
  6. washwashed with water
  7. customdried overnight at 50-60° C.

Sources & evidence

ORD record
ord-aa206e7fff2a4b8087663e11c57e0c05
Source dataset
uspto-grants-2003_07
Patent number
US06600073B1

Reaction notes

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