Sodium Hydroxide → Sertraline

HRID 1359606Notes

Reaction equation

HRID 1359606 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 68617Sertraline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Sertraline base for use in the processes of the present invention may be produced by dissolving sertraline mandelate in ethyl acetate followed by neutralization of the sertraline mandelate with aqueous sodium hydroxide. The organic phase is separated from the aqueous phase and dried using magnesium sulfate. The solvent is removed under reduced pressure to produce sertraline base as an oil. Methods for making sertraline base are set forth in U.S. Pat. Nos. 4,536,518 and 5,248,699, the contents of which are incorporated herein by reference.

Workup

  1. customThe organic phase is separated from the aqueous phase
  2. customdried
  3. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-5f121581e7994527b89daa1554f3244a
Source dataset
uspto-grants-2003_07
Patent number
US06600073B1

Reaction notes

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