Ethanol → 3-(Dimethylamino)-1-phenyl-1-propanone

HRID 1422652Notes

Reaction equation

HRID 1422652 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[NH:10]([CH3:12])[CH3:11].Cl.[CH3:14]CO>>[CH3:11][N:10]([CH3:14])[CH2:12][CH2:2][C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 3

HCID 702EthanolHCID 7410AcetophenoneHCID 10473Dimethylamine, hydrochloride

Product 1

HCID 770423-(Dimethylamino)-1-phenyl-1-propanoneYield 40%

Procedure

The solution of acetophenone (30 g, 0.25 mol) and Me2NH.HCl (0.28 mol) in EtOH (400 mL) was heated at 70° C. overnight. The resulting mixture was concentrated and the residue was washed with EtOAc to give 3-(dimethylamino)-1-phenylpropan-1-one (17.7 g, 40%). 1H NMR (400 MHz, CDCl3): δ=2.36 (m, 6H), 2.74 (m, 2H), 3.14 (m, 2H), 7.43 (m, 2H), 7.52 (m, 1H), 7.94 (m, 2H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. washthe residue was washed with EtOAc

Sources & evidence

ORD record
ord-53e887d83d494ef99a6c0bbf89ce55b8
Source dataset
uspto-grants-2015_01
Patent number
US08927539B2

Reaction notes

Loading…