HCID 523006, compound → Sertraline Hydrochloride

HRID 853176Notes

Reaction equation

HRID 853176 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].CC(N(C)C)=O>C(C(C)=O)C(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 523006HCID 523006, compoundHCID 131718189(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate

Product 1

HCID 63009Sertraline HydrochlorideYield 94.1%

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
80 °C

Procedure

A suspension of 2 g sertraline mandelate in 40 ml methyl isobutyl ketone is heated at 80° C. and 0.6 g dimethylacetamide hydrochloride in solid form is added. The suspension is stirred at 80° C. for 30 minutes and then cooled down to room temperature. After stirring for about one hour, the product is filtered off and dried at 50° C. under vacuum to yield 1.41 g (94%) of sertraline hydrochloride Form II.

Workup

  1. temperaturecooled down to room temperature
  2. stirringAfter stirring for about one hour
  3. filtrationthe product is filtered off
  4. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-358e9b22b6b34ebca7b85e99b7c23c54
Source dataset
uspto-grants-2007_08
Patent number
US07253320B2

Reaction notes

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