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

HRID 235240Notes

Reaction equation

HRID 235240 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>[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

3

Reactant 1

HCID 11586813(2-Acetamidophenyl) cyclohexyl methanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

A solution of (2-acetamidophenyl) cyclohexyl methanone (0.53 g, 2.16 mmol) in methanol (5 ml) and concentrated hydrochloric add (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, 91%) as a white solid. mp 73°-75° C. 1H NMR (360 MHz, CDCL3)-- 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. additionadd (15 ml)
  2. temperatureAfter this time the solution was cooled to ambient temperature
  3. customthe solvents removed in vacuo
  4. dissolutionThe residue was dissolved in water (10 ml)
  5. extractionThe mixture was then extracted into ethyl acetate (4×20 ml)
  6. dry with materialdried (MgSO4)
  7. customThe solvent was evaporated
  8. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-b1e787aae57f427598a3ad39411cde6d
Source dataset
uspto-grants-1997_01
Patent number
US05597915

Reaction notes

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