(2-Acetamidophenyl) cyclohexyl methanone → (2-Aminophenyl)(cyclohexyl)methanone

HRID 1490098Notes

Reaction equation

HRID 1490098 reaction equation
C([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:12])(=O)C>CO.Cl>[NH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]([CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1)=[O:12]

Participants

4

Reactant 1

HCID 11586813(2-Acetamidophenyl) cyclohexyl methanone

Product 1

HCID 15634733(2-Aminophenyl)(cyclohexyl)methanoneYield 91.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of (2-acetamidophenyl) cyclohexyl methanone (0.53 g) in methanol (5 ml) and concentrated hydrochloric acid (15 ml) was heated at 80° C. for 1 hour. After this time the solution was cooled to ambient temperature and the solvents removed in vacuo. The residue was dissolved in water (10 ml) and basified with 4N sodium hydroxide solution (20 ml). The mixture was then extracted into ethyl acetate (4×20 ml) and the organic layers combined and dried (MgSO4). The solvent was evaporated and the residue chromatographed on silica gel using petrol:ethyl acetate (2:1), to afford the title compound (0.40 g) as a solid. The spectroscopic properties of this material were identical to those described in Method A.

Workup

  1. customthe solvents removed in vacuo
  2. dissolutionThe residue was dissolved in water (10 ml)
  3. extractionThe mixture was then extracted into ethyl acetate (4×20 ml)
  4. dry with materialdried (MgSO4)
  5. customThe solvent was evaporated
  6. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-dc748a3bf96d4ed99180ec254ab8785e
Source dataset
uspto-grants-1997_10
Patent number
US05681833

Reaction notes

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