Acetone → N-Cyclohexyl-N-hydroxycyclohexanamine

HRID 359581Notes

Reaction equation

HRID 359581 reaction equation
[CH:1]1([NH:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CC(C)=[O:16]>>[CH:8]1([N:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[OH:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

3

Reactant 2

HCID 180Acetone2×HCID 7582Dicyclohexylamine

Product 1

HCID 13464777N-Cyclohexyl-N-hydroxycyclohexanamineYield 82.6%

Procedure

A solution of 0.057 M DMD in acetone (49.2 ml, 3.317 mmol) was added to a cold stirred solution of N,N-dicyclohexylamine (Kodak; 0.508 g, 3.317 mmol) in acetone (5 ml). The reaction mixture was stirred for ten minutes in an ice bath. The solution was dried over Na2SO4, filtered, and the solvent removed in vacuo to give a colorless crystalline solid. This solid was purified by flash chromatography on silica gel with ethyl acetate:petroleum ether (20:80) elution to give a white crystalline solid (0.457 g, 82.6% yield), mp 70-72.

Workup

  1. dry with materialThe solution was dried over Na2SO4
  2. filtrationfiltered
  3. customthe solvent removed in vacuo
  4. customto give a colorless crystalline solid
  5. customThis solid was purified by flash chromatography on silica gel with ethyl acetate:petroleum ether (20:80) elution

Sources & evidence

ORD record
ord-d74587dfb19849b981e4caa4c1d1bf4b
Source dataset
uspto-grants-1991_03
Patent number
US05001233

Reaction notes

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