Hydrochloric Acid → Sertraline Hydrochloride

HRID 2111045Notes

Reaction equation

HRID 2111045 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
42.5 °C

Procedure

Sertraline free base (5 gm) is dissolved in isoamyl alcohol (35 ml) at 25-30° C., heated to 40-45° C., pH of the mass is adjusted to 2.0 with conc. hydrochloric acid (36%) at 40-45° C. and then stirred for 3 hours 30 minutes at 45-48° C. Filtered the solid and dried for 15 hours at 60° C. to give 2.5 gm of sertraline hydrochloride crystalline form II.

Workup

  1. filtrationFiltered the solid
  2. customdried for 15 hours at 60° C.

Sources & evidence

ORD record
ord-eb07460740d94096b5745112b6563b6f
Source dataset
uspto-grants-2009_04
Patent number
US07518019B2

Reaction notes

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