Acetyl chloride → 6-Acetylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one

HRID 1769990Notes

Reaction equation

HRID 1769990 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:11](=[O:12])[CH:10]=[CH:9][CH2:8][CH2:7]1.C(N(CC)CC)C>ClCCl>[C:1]([NH:5][C:6]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:11](=[O:12])[CH:10]=[CH:9][CH2:8][CH2:7]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 162835Dehydronorketamine

Product 1

HCID 200966006-Acetylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (142 μl, 1.8 mmol) was added to a solution of 6-amino-6-(2-chlorophenyl)-2-cyclohexen-1-one (R. F. Parceli and J. P. Sanchez, J. Org. Chem., 46:5055 [1981]), (200 mg, 0.9 mmol) and triethylamine (1.0 ml) in dichloromethane (10 ml), and the reaction stirred at room temperature for 1 h. Analysis by TLC indicated complete reaction, and the mixture was partitioned between ethyl acetate and 1N HCI. The organic phase was washed with brine, dried (MgSO4), and the solvent removed by evaporation. Flash chromatography on silica gel eluted with 1:1 ethyl acetate/hexane afforded 6-acetylamino-6-(2-chlorophenyl)-2-cyclohexen-1-one which crystallized on standing, m.p. 144°-145° C.

Workup

  1. customreaction
  2. customthe mixture was partitioned between ethyl acetate and 1N HCI
  3. washThe organic phase was washed with brine
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed by evaporation
  6. washFlash chromatography on silica gel eluted with 1:1 ethyl acetate/hexane

Sources & evidence

ORD record
ord-e38ed7566ec048d1830bf9515e619277
Source dataset
uspto-grants-1995_01
Patent number
US05384331

Reaction notes

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