Water → Sertraline

HRID 502018Notes

Reaction equation

HRID 502018 reaction equation
O.C(O)(=O)C(C1C=CC=CC=1)O.[Cl:13][C:14]1[CH:15]=[C:16]([C@H:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[C@@H:24]([NH:31][CH3:32])[CH2:23][CH2:22]2)[CH:17]=[CH:18][C:19]=1[Cl:20].[OH-].[Na+]>C(OCC)(=O)C>[CH3:32][NH:31][C@@H:24]1[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:30]=2[C@H:21]([C:16]2[CH:17]=[CH:18][C:19]([Cl:20])=[C:14]([Cl:13])[CH:15]=2)[CH2:22][CH2:23]1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 1047927879617-97-3

Product 1

HCID 68617Sertraline

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
14 °C

Procedure

Water (30 ml) and ethyl acetate (35 ml) are added to (1S-cis)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalenamine mandelate (obtained in step-Ia), cooled to 10-18° C. and aqueous sodium hydroxide (50%) is slowly added for 1 hour 30 minutes at 10-18° C. (to adjust the pH to 9.5-11.0). The contents are stirred for 30-45 minutes, separated the aqueous layer and discarded it. Activated carbon (0.25 gm) is added to the reaction mass, stirred for 15-30 minutes, filtered and washed with ethyl acetate (5 ml). Distilled off ethyl acetate under reduced pressure until the mass temperature reaches to 50-55° C. to give 3.1 gm of sertraline free base as residue (HPLC purity: 99.7%).

Workup

  1. customseparated the aqueous layer
  2. additionActivated carbon (0.25 gm) is added to the reaction mass
  3. stirringstirred for 15-30 minutes
  4. filtrationfiltered
  5. washwashed with ethyl acetate (5 ml)
  6. distillationDistilled off ethyl acetate under reduced pressure until the mass temperature
  7. customreaches to 50-55° C.

Sources & evidence

ORD record
ord-da9c73d19a5542818dba8313a82e7f2b
Source dataset
uspto-grants-2010_08
Patent number
US07772438B2

Reaction notes

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