Methanol → Sertraline Hydrochloride

HRID 1393720Notes

Reaction equation

HRID 1393720 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].CO.[H][H]>[Ni].ClC1C=CC=CC=1Cl>[ClH:1].[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

6

Reactant 3

HCID 887MethanolHCID 9796475N-(4-(3,4-Dichlorophenyl)-3,4-dihydro-1(2H)-naphthalenylidene)methanamineHCID 178418361HCID 178418361, compound

Product 1

HCID 63009Sertraline Hydrochloride

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

N-[4-(3,4-dichlorophenyl)-3,4-dihydro-1(2H)naphthalenylidene]methanamine (Ketimine) (50 g), methanol (300 ml), Raney Nickel (0.15 g wet basis) and o-dichlorobenzene (50 ml) are charged into a reaction vessel. The mixture is hydrogenated at 5 to 6 kg/cm2 over pressure of hydrogen for 6 to 7 hrs at about 28° C. to 30° C. The catalyst is removed by filtration and the cake is washed with 50 ml methanol. The cis to trans ratio is 87 to 89/9 to 13. The amount of dehalogenated by product is <0.1%.

Workup

  1. customThe catalyst is removed by filtration
  2. washthe cake is washed with 50 ml methanol

Sources & evidence

ORD record
ord-eb37fb60c0b44636960c8839cf6493f6
Source dataset
uspto-grants-2008_03
Patent number
US07345201B2

Reaction notes

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