Cyclohexylamine → HCID 289865, compound

HRID 2235255Notes

Reaction equation

HRID 2235255 reaction equation
[OH:1][CH:2]1[C:6]([CH3:8])([CH3:7])[CH2:5]C[C:3]1=[O:9].[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1.O.C1(C)C(S(O)(=O)=[O:25])=CC=CC=1>CCO>[CH:10]1([NH:16][C:3](=[O:9])[CH:2]([OH:1])[C:6]([CH3:7])([CH3:8])[CH2:5][OH:25])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 7965CyclohexylamineHCID 124969952-Methylbenzenesulfonic acid hydrateHCID 53645448HCID 53645448, compound

Product 1

HCID 289865HCID 289865, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

Place 2-hydroxy-3,3-dimethyl-cyclopentanone (1.044 g, 7.86 mmol), cyclohexylamine (1.91 ml, 16.51 mmol) and toluenesulfonic acid monohydrate (0.152 g, 0.1 mmol) in EtOH (4 mL) in a microwave reactor. Stir for 1 hour at 150° C. Quench with 1N HCl and extract with ethyl acetate. Wash the extract with NaHCO3, brine. Dry over magnesium sulfate, filter, and concentrate to afford N-cyclohexyl-2,4-dihydroxy-3,3-dimethyl-butyramide.

Workup

  1. customQuench with 1N HCl
  2. extractionextract with ethyl acetate
  3. washWash the
  4. extractionextract with NaHCO3, brine
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-97a5dda0d18c43b6a17d06eeefbf8222
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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