Water → Sertraline, cis-(-)-

HRID 502017

Reaction equation

HRID 502017 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12](=[N:19][CH3:20])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8].O>[Pd].C([O-])([O-])=O.[Ca+2].CO>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C@H:12]([NH:19][CH3:20])[CH2:11][CH2:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 962WaterHCID 9796475N-(4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene)methanamine

Product 1

HCID 54375Sertraline, cis-(-)-

Reagents, catalysts & solvents 2

HCID 12000666Calcium Palladium CarbonateCatalystHCID 887MethanolSolvent

Procedure

The mixture of 4-(3,4-Dichlorophenyl)-3,4-dihydro-N-methyl-1 (2H)-naphthalenimine (10 gm), 5% Pd/CaCO3 (grade-21, 0.6 gm), water (2 ml) and methanol (150 ml) is taken in a hydrogenation flask and then subjected to hydrogenation under a hydrogen pressure of 0.5 Kg at 20-35° C. for 3 hours 30 minutes. The catalyst is removed by filtration and the solvent is evaporated completely under vacuum to obtain cis-(+)-4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydro-N-methyl-naphthalenamine. (cis-(+):trans-(+):99.8:0.2).

Workup

  1. customis taken in a hydrogenation flask
  2. customat 20-35° C.
  3. customfor 3 hours
  4. custom30 minutes
  5. customThe catalyst is removed by filtration
  6. customthe solvent is evaporated completely under vacuum

Sources & evidence

ORD record
ord-6be54985a7174589b149d66c4e7b4b7a
Source dataset
uspto-grants-2010_08
Patent number
US07772438B2

Linked notes

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