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

HRID 1655670Notes

Reaction equation

HRID 1655670 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-cyclohexene-1-one (R. F. Parcell 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 HCl. 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 HCl
  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-8c6d9069ea4f4dc98dff23bfa023deb8
Source dataset
uspto-grants-1993_10
Patent number
US05250732

Reaction notes

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