Hydrochloric Acid → Sertraline Hydrochloride

HRID 2111047Notes

Reaction equation

HRID 2111047 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]>C(O)CC(C)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:21]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68617Sertraline

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 1

HCID 31260Isoamyl AlcoholSolvent

Conditions

Temperature
15 °C

Procedure

Sertraline free base (10 gm) is dissolved in isoamyl alcohol (70 ml) at 25-30° C., cooled to 15° C. and then pH of the mass is adjusted to 2.0 with conc. hydrochloric acid (36%) at 10-15° C. The mass temperature is raised to 25° C., stirred for 2 hours at 25-30° C. and then filtered the solid. Diisopropyl ether is added to the resulting wet solid at 25-30° C. and stirred for 20 minutes at 25-30° C. Filtered the solid and dried for 2 hours at 60° C. to give 7.3 gm of sertraline hydrochloride crystalline form II.

Workup

  1. temperatureThe mass temperature is raised to 25° C.
  2. filtrationfiltered the solid
  3. additionDiisopropyl ether is added to the resulting wet solid at 25-30° C.
  4. stirringstirred for 20 minutes at 25-30° C
  5. filtrationFiltered the solid
  6. customdried for 2 hours at 60° C.

Sources & evidence

ORD record
ord-17caec9eadcf4706a6ef1e21440d7857
Source dataset
uspto-grants-2009_04
Patent number
US07518019B2

Reaction notes

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