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

HRID 743690Notes

Reaction equation

HRID 743690 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 h. 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 amine (0.40 g). Mp 73°-75° C. 1H NMR (360 MHz, CDCl3) δ 1.23-2.09 (10H, m), 3.27 (1H, m), 6.29 (2H, brs), 6.64 (2H, m), 7.25 (1H, dt, J=6 and 1 Hz), 7.76 (1H, dd, J=7 and 1 Hz).

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-022f1163340948d38232dd063508c680
Source dataset
uspto-grants-1996_09
Patent number
US05556969

Reaction notes

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