Hydrochloric Acid → Sertraline Hydrochloride

HRID 1794662Notes

Reaction equation

HRID 1794662 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-94849ce7c0d14ac1b91e5a90bafaf8af
Source dataset
uspto-grants-2006_04
Patent number
US07022881B2

Reaction notes

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