4-Phenylcyclohexanone → HCID 178511499, compound

HRID 1249746Notes

Reaction equation

HRID 1249746 reaction equation
C([O-])=O.[NH4+].[C:5]1([CH:11]2[CH2:16][CH2:15][C:14](=O)[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C([BH3-])#[N:19].[Na+]>CO.C(Cl)Cl>[C:5]1([C@H:11]2[CH2:16][CH2:15][C@H:14]([NH2:19])[CH2:13][CH2:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 786054-PhenylcyclohexanoneHCID 2723923Ammonium formateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 178511499HCID 178511499, compoundYield 68.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Ammonium formate (18 g, 285 mmol) was added to a solution of 4-phenylcyclohexanone (5 g, 28.7 mmol) in methanol (150 ml) under nitrogen at room temperature followed by the portionwise addition of sodium cyanoborohydride (1.85 g, 29.4 mmol). After stirring the reaction mixture at room temperature for 24 hours, the methanol was removed under vacuum to leave an oily residue. The residue was dissolved in methylene chloride (100 ml) which was then washed with 1N sodium hydroxide (2×100 ml). The organic layer was separated, dried over sodium sulfate, filtered and concentrated to leave an off-white solid. Purification by flash chromatography (silica gel, 0-20% methanol/methylene chloride) provided 3.46 g of trans-4-phenyl-cyclohexylamine as a white solid.

Workup

  1. customthe methanol was removed under vacuum
  2. customto leave an oily residue
  3. washwas then washed with 1N sodium hydroxide (2×100 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto leave an off-white solid
  9. customPurification by flash chromatography (silica gel, 0-20% methanol/methylene chloride)

Sources & evidence

ORD record
ord-29d34f9e291048429834a73f80516701
Source dataset
uspto-grants-2002_01
Patent number
US06335324B1

Reaction notes

Loading…