Methane → HCID 178511500, compound

HRID 657618Notes

Reaction equation

HRID 657618 reaction equation
C([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:11][CH2:10]1)C1C=CC=CC=1.C>CO.[Pd]>[OH:21][C:18]1[CH:17]=[CH:16][C:15]([C@H:12]2[CH2:13][CH2:14][C@H:9]([NH2:8])[CH2:10][CH2:11]2)=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 297MethaneHCID 178516052HCID 178516052, compound

Product 1

HCID 178511500HCID 178511500, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of trans-N-benzyl-4-(4-hydroxyphenyl)cyclohexanamine (7.69 g) and palladium over charcoal (800 mg) in methanol (300 mL) is stirred at a temperature close to 40° C. for 8 h under a pressure of 15 bar of dihydrogene. Filtration over celite and evaporation of the solvent under reduced pressure affords 4.9 g of trans-4-(4-hydroxyphenyl)cyclohexanamine as a white powder. trans-N-benzyl-4-(4-hydroxyphenyl)cyclohexanamine can be prepared as described in WO 01/81295 (Warner-Lambert Company).

Workup

  1. customclose to 40° C. for 8 h under a pressure of 15 bar of dihydrogene
  2. filtrationFiltration
  3. customover celite and evaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-464b1abb435847e989abac0c4f81eeee
Source dataset
uspto-grants-2011_12
Patent number
US08076329B2

Reaction notes

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