Cyclohexanone → HCID 419885, compound

HRID 1856752Notes

Reaction equation

HRID 1856752 reaction equation
[NH2:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[C:7]1(=O)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[H][H]>C(O)C.[C].[Pd]>[OH:6][CH:3]([CH2:4][CH3:5])[CH2:2][NH:1][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 261071-Amino-2-butanolHCID 178418361HCID 178418361, compound

Product 1

HCID 419885HCID 419885, compoundYield 96.8%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1-Amino-2-butanol (120 g) is added dropwise into a solution of cyclohexanone (132 g) in ethanol (600 ml) at room temperature, and the mixture is stirred at room temperature for one day. To the reaction solution is added 10% palladium-carbon (6 g), and the mixture is subjected to catalytic hydrogenation at 60° C. under 4 atms of hydrogen gas. The catalyst is removed by filtration, and the filtrate is concentrated under reduced pressure, and distilled under reduced pressure to give N-(2-hydroxybutyl)-N-cyclohexylamine (223 g) as a colorless oil.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-e181d15f6790470dad5014839e6406ba
Source dataset
uspto-grants-2000_11
Patent number
US06143763

Reaction notes

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