p-Aminoacetophenone → HCID 788567, compound

HRID 2186769Notes

Reaction equation

HRID 2186769 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3].ON1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2N=N1.C([O:24][CH2:25][CH3:26])(=O)C>ClCCl>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:25](=[O:24])[CH:26]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:1]

Participants

5

Reactant 3

HCID 7468p-AminoacetophenoneHCID 8857Ethyl AcetateHCID 757711-Hydroxybenzotriazole

Product 1

HCID 788567HCID 788567, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
23 °C

Procedure

1-(3-Dimethylamino)propyl-3-ethylcarbodiimide hydrochloride (EDC, 210 mg, 1.1 mmol, 1.2 equiv) was added to a solution of acid (190 mg, 0.91 mmol, 1.0 equiv), 4-aminoacetophenone (120 mg, 0.91 mmol, 1.0 equiv) and 1-hydroxybenzotriazole (HOBT, 190 mg, 1.4 mmol, 1.5 equiv) in dichloromethane at 23° C. The reaction mixture was stirred at 23° C. for 18 hours, diluted with ethyl acetate (50 mL), washed once with 1N sodium hydroxide (25 mL) and once with 1N hydrochloric acid (25 mL). The organics were dried over magnesium sulfate and concentrated. The residue was purified by flash column chromatography (25% THF/hexanes) to provide N-(4-Acetyl-phenyl)-2,2-diphenyl-acetamide (140 mg). MS: 330 (M+1)

Workup

  1. washwashed once with 1N sodium hydroxide (25 mL) and once with 1N hydrochloric acid (25 mL)
  2. dry with materialThe organics were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography (25% THF/hexanes)

Sources & evidence

ORD record
ord-be97b003b8d04dba8f58450a3a9ee08e
Source dataset
uspto-grants-2002_06
Patent number
US06407120B1

Reaction notes

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