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

HRID 1655000Notes

Reaction equation

HRID 1655000 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, 2.16mmol) 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 in 2:1 petrol:ethyl acetate, to afford the amine (0.40 g, 91%) as a white solid. mp 73°-75° C. 1H NMR (360MHz, CDCl3) δ1.23-2.09 (10H, m), 3.27 (1H, m), 6.29 (2H, brs), 6.64 (2H, m), 7.25 (1H, dt, J=6 and 1Hz), 7.76 (1H, dd, J=7 and 1Hz).

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 in 2:1 petrol

Sources & evidence

ORD record
ord-45beb6974694445090bf632d8aa566ce
Source dataset
uspto-grants-1995_04
Patent number
US05410049

Reaction notes

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