HCID 14674417, compound → Venlafaxine

HRID 2249306Notes

Reaction equation

HRID 2249306 reaction equation
[CH3:1][N:2]([CH3:21])[C:3](=S)[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>O1CCOCC1.C(O)(=O)C.[Ni]>[CH3:1][N:2]([CH2:3][CH:4]([C:5]1([OH:11])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)[CH3:21]

Participants

4

Reactant 1

HCID 14674417HCID 14674417, compound

Product 1

HCID 5656Venlafaxine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 22565020HOAc dioxaneSolvent

Procedure

A solution of N,N-dimethyl-α-(1-hydroxycyclohexyl)-p-methoxyphenylthioacetamide in 5 ml per gram of thioamide in dioxan/acetic acid (9:1) is added to Raney nickel (20 grams per gram of thioamide) in 50 ml per gram of the thioamide of the same solvent at room temperature to 50° C. After 15 minutes to 10 hours the Raney nickel is filtered through kieselguhr and the solvent is evaporated under reduced pressure. The residue is partitioned between 2N sodium hydroxide solution and methylene chloride. The organic phase is dried and the solvent is evaporated. The residue is converted into the hydrochloride salt of the title compound using 4N isopropanolic hydrogen chloride.

Workup

  1. filtrationAfter 15 minutes to 10 hours the Raney nickel is filtered through kieselguhr
  2. customthe solvent is evaporated under reduced pressure
  3. customThe residue is partitioned between 2N sodium hydroxide solution and methylene chloride
  4. customThe organic phase is dried
  5. customthe solvent is evaporated

Sources & evidence

ORD record
ord-c48a56cb75904ece98666af5cc60ad2b
Source dataset
uspto-grants-1991_08
Patent number
US05043466

Reaction notes

Loading…