Hydrochloric Acid → Sertraline Hydrochloride

HRID 502016Notes

Reaction equation

HRID 502016 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.C([O-])(=O)C(C1C=CC=CC=1)O.[ClH:32]>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:32]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131718189(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Conditions

Temperature
27.5 °C

Procedure

Sertraline mandelate (10 gm) is suspended in tert-amyl alcohol (65 ml) at 25-30° C., pH of the mass is adjusted to 2.0 with conc. hydrochloric acid (36%) at 25-30° C. and then stirred for 8 hours at 25-30° C. Filtered the solid and dried at 60° C. for 3 hours 30 minutes to give 4.3 gm of sertraline hydrochloride crystalline form II.

Workup

  1. filtrationFiltered the solid
  2. customdried at 60° C. for 3 hours 30 minutes

Sources & evidence

ORD record
ord-7122467702b94d5ba30e3de22736d8a7
Source dataset
uspto-grants-2010_08
Patent number
US07772437B2

Reaction notes

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