1-[2-(Dimethylamino)-1-[4-(phenylmethoxy)phenyl]ethyl]cyclohexanol → Desvenlafaxine

HRID 1874315Notes

Reaction equation

HRID 1874315 reaction equation
[CH3:1][N:2]([CH3:26])[CH2:3][CH:4]([C:19]1([OH:25])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)[C:5]1[CH:10]=[CH:9][C:8]([O:11]CC2C=CC=CC=2)=[CH:7][CH:6]=1>CO.[Pd]>[CH3:26][N:2]([CH3:1])[CH2:3][CH:4]([C:19]1([OH:25])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 201299231-[2-(Dimethylamino)-1-[4-(phenylmethoxy)phenyl]ethyl]cyclohexanol

Product 1

HCID 125017DesvenlafaxineYield 81.08%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1-[2-(Dimethylamino)-1-(4-benzyloxyphenyl)ethyl]cyclohexanol (30 g) was dissolved in methanol (600 ml), charged with 10% palladium on carbon (3 g) and hydrogenated pressure for 6 h at room temperature. The catalyst was filtered, washed with methanol, and combined filtrate evaporated under reduced pressure to give 18 g (81.08%) of the 1-[2-(dimethylamino)-1-(4-hydroxyphenyl)ethyl]cyclohexanol.

Workup

  1. filtrationThe catalyst was filtered
  2. washwashed with methanol
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-03b2eb875dc24d14894102cbef2bda7f
Source dataset
uspto-grants-2012_11
Patent number
US08304578B2

Reaction notes

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