4-tert-Butylcyclohexanone → HCID 178445680, compound

HRID 1003782Notes

Reaction equation

HRID 1003782 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][C:8](=O)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]1([CH:26]([NH2:28])[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[H][H]>C(O)CO.C(OCC)(=O)C>[CH2:12]([NH:19][C@H:8]1[CH2:9][CH2:10][C@@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[C:20]1([CH:26]([NH:28][C@H:8]2[CH2:9][CH2:10][C@@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]2)[CH3:27])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 73924-tert-ButylcyclohexanoneHCID 74081-Phenethylamine2×HCID 7504Benzylamine2×HCID 178418361HCID 178418361, compound

Product 2

HCID 178445680HCID 178445680, compoundHCID 178464518HCID 178464518, compound

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Equimolar amounts of 4-tert-butylcyclohexanone and benzylamine or 1-phenylethylamine are vigorously stirred in the solvent in question in the presence of a catalyst and in an atmosphere of pure hydrogen. Once no more benzylamine or 1-phenylethylamine can be detected by taking samples, 200 ml of ethyl acetate are added if the solvent used is ethylene glycol. The reaction mixture is washed three times with water, filtered, dried over MgSO4 and concentrated under reduced pressure. If other solvents are used, the reaction mixture is filtered off directly after the reaction has ended, the catalyst is washed with methanol and the filtrate is concentrated under reduced pressure. In each case, the crude product has the cis-selectivity stated in Table 1 (determination by HPLC). Crystallization of the hydrochlorides or purification by column chromatography (silica gel, ethyl acetate) gives pure N-benzyl-cis-4-tert-butyl-cyclohexylamine or pure N-(1-phenylethyl)-cis-4-tert-butyl-cyclohexylamine.

Workup

  1. additionare added if the solvent
  2. washThe reaction mixture is washed three times with water
  3. filtrationfiltered
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. filtrationthe reaction mixture is filtered off directly after the reaction
  7. washthe catalyst is washed with methanol
  8. concentrationthe filtrate is concentrated under reduced pressure
  9. customCrystallization of the hydrochlorides or purification by column chromatography (silica gel, ethyl acetate)

Sources & evidence

ORD record
ord-e068822dd50c4bb089aa86dbd65758ca
Source dataset
uspto-grants-2000_04
Patent number
US06046360

Reaction notes

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