Acetyl bromide → N-Formyl-3-(4-acetylphenyl)-1,1-dimethylpropanamine

HRID 1105633Notes

Reaction equation

HRID 1105633 reaction equation
[CH:1]([NH:3][C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:2].[C:15](Br)(=[O:17])[CH3:16].[Cl-].[Al+3].[Cl-].[Cl-]>ClCCCl>[CH:1]([NH:3][C:4]([CH3:14])([CH3:13])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:15](=[O:17])[CH3:16])=[CH:9][CH:8]=1)=[O:2]

Participants

5

Reactant 3

HCID 10482Acetyl bromideHCID 6451240Aluminum(III) ChlorideHCID 54547819N-Formyl-3-phenyl-1, 1-dimethylpropanamine

Product 1

HCID 20556108N-Formyl-3-(4-acetylphenyl)-1,1-dimethylpropanamine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-Formyl-3-phenyl-1, 1-dimethylpropanamine (115 g) was dissolved in 1,2-dichloroethane (850 ml) at 0° C. Acetyl bromide (116 ml) was added followed by the portionwise addition of aluminum chloride (263 g) over 0.5 h. At the end of addition the mixture was allowed to warm to room temperature and then refluxed for 1h. The hot solution was poured onto crushed ice (3 Kg) and the mixture extracted with chloroform. The chloroform extracts were washed with water, sodium bicarbonate and dried (MgSO4). Evaporation of the solvent gave an oil of which 25 g was chromatographed on Kieselgel 60 (1 Kg). Elution with 1% methanol-chloroform gave the title compound as an oil (18 g). τ(CDCl3) 8.6 (6H, s) 8.4-7.75 (2H, m), 7.45 (3H, s), 7.5-7.05 (2H, m), 3.0-4.0 (1H, broad), 2.7 (2H, d, J=8 Hz), 2.15 (2H, d, J=8 Hz) 1.2 (1H, d, J=5 Hz).

Workup

  1. additionAt the end of addition the mixture
  2. temperaturerefluxed for 1h
  3. additionThe hot solution was poured
  4. extractionthe mixture extracted with chloroform
  5. washThe chloroform extracts were washed with water, sodium bicarbonate
  6. dry with materialdried (MgSO4)
  7. customEvaporation of the solvent
  8. customgave an oil of which 25 g
  9. customwas chromatographed on Kieselgel 60 (1 Kg)
  10. washElution with 1% methanol-chloroform

Sources & evidence

ORD record
ord-2856fc2ef2df4d98b59158e5e2536906
Source dataset
uspto-grants-1982_01
Patent number
US04309443

Reaction notes

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