Hydrochloric Acid → Sertraline Hydrochloride

HRID 1367752Notes

Reaction equation

HRID 1367752 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.O.[ClH:22]>C(O)(=O)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:22]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 68617Sertraline

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

300 gms of sertraline base is dissolved in 600 ml acetic acid at room temperature and stirred to obtain a clear solution. To the above clear solution, 3000 ml water is added under stirring in 20 min at 25° C. The reaction mixture is cooled to 5°-10° C. and stirred for 1 hr. Concentrated hydrochloric acid is added to the above clear solution and the pH adjusted to between 1 to 2 at 5-10° C. The reaction mixture is stirred for 15 minutes and the sertraline hydrochloride precipitates during this period. 600 ml of water is charged and the reaction mixture is stirred at 10-15° C., for 1 hour. The solids are filtered and dried in a fluid bed dryer at 60-70° C. for 4-5 hrs to give Form V of sertraline hydrochloride Form V of sertraline hydrochloride.

Workup

  1. customto obtain a clear solution
  2. stirringunder stirring in 20 min at 25° C
  3. temperatureThe reaction mixture is cooled to 5°-10° C.
  4. stirringstirred for 1 hr
  5. customadjusted to between 1 to 2 at 5-10° C
  6. stirringThe reaction mixture is stirred for 15 minutes
  7. customthe sertraline hydrochloride precipitates during this period
  8. addition600 ml of water is charged
  9. stirringthe reaction mixture is stirred at 10-15° C., for 1 hour
  10. filtrationThe solids are filtered
  11. customdried in a fluid bed dryer at 60-70° C. for 4-5 hrs

Sources & evidence

ORD record
ord-7b2f28750d294197b162fb67ba237cd3
Source dataset
uspto-grants-2011_02
Patent number
US07893300B2

Reaction notes

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