Sodium Hydroxide → Sertraline

HRID 1794660Notes

Reaction equation

HRID 1794660 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.[OH-].[Na+]>C(OCC)(=O)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

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131718189(1S,4S)-4-(3,4-dichlorophenyl)-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine;2-hydroxy-2-phenylacetate2×

Product 1

HCID 68617SertralineYield 95.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sertraline mandelate (5 g) was stirred at room temperature with 50 mL ethyl acetate. Aqueous sodium hydroxide was added dropwise until the sertraline mandelate was completely neutralized. The phases were separated and the organic phase was dried over MgSO4 and filtered. The solvent was removed under reduced pressure resulting sertraline base as an oil (3.2 g).

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-77edd810b18c4df8a6e10888241a1ae9
Source dataset
uspto-grants-2006_04
Patent number
US07022881B2

Reaction notes

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