Hydrochloric Acid → Sertraline Hydrochloride

HRID 460498Notes

Reaction equation

HRID 460498 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)CCC>[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 2631-ButanolSolvent

Procedure

Sertraline mandelate (20 g) and n-butanol were stirred at room temperature. The mixture was acidified with hydrogen chloride until pH 0 was reached. During the acidification the temperature of the reaction mixture rose to ˜50° C. After the natural cooling to room temperature, the mixture was stirred at room temperature for two hours. The solid was filtrated, washed with n-butanol and dried at 80° C. to afford sertraline hydrochloride Form II (9.02 g).

Workup

  1. customrose to ˜50° C
  2. filtrationThe solid was filtrated
  3. washwashed with n-butanol
  4. customdried at 80° C.

Sources & evidence

ORD record
ord-934e12029bdf47abbb10afff3d8d626c
Source dataset
uspto-grants-2007_03
Patent number
US07196222B2

Reaction notes

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