Potassium Carbonate → 1-(3-Bromophenyl)-2-(diallylamino)ethanone

HRID 876714Notes

Reaction equation

HRID 876714 reaction equation
C(=O)([O-])[O-].[K+].[K+].[Br:7][C:8]1[CH:9]=[C:10]([CH:15]=[CH:16][CH:17]=1)[C:11](=[O:14])[CH2:12]Br.[CH2:18]([NH:21][CH2:22][CH:23]=[CH2:24])[CH:19]=[CH2:20]>C(#N)C>[Br:7][C:8]1[CH:9]=[C:10]([C:11](=[O:14])[CH2:12][N:21]([CH2:22][CH:23]=[CH2:24])[CH2:18][CH:19]=[CH2:20])[CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 31279DiallylamineHCID 5195852-Bromo-1-(3-bromophenyl)ethan-1-one

Product 1

HCID 867627501-(3-Bromophenyl)-2-(diallylamino)ethanoneYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Potassium carbonate (38.8 g, 281 mmol) is added to 3-bromophenacyl bromide (60 g 216 mmol) in acetonitrile (430 mL), and the mixture is cooled under nitrogen to 0° C. Diallylamine (34.6 mL, 280.63 mmol) is added drop wise over 1 hour and the reaction is allowed to warm to 22° C. overnight. The crude reaction mixture is concentrated and the residue is partitioned in water (300 mL) and MTBE (300 mL). The aqueous layer is discarded and the organic layer is washed with water (100 mL, 2×) and with brine (100 mL). The organic layer is dried over sodium sulfate, filtered, and the solvent evaporated to constant weight to give the title compound (62 g, 98%). ES/MS (m/e): 294 (M+1).

Workup

  1. temperatureto warm to 22° C. overnight
  2. customThe crude reaction mixture
  3. concentrationis concentrated
  4. customthe residue is partitioned in water (300 mL)
  5. washthe organic layer is washed with water (100 mL, 2×) and with brine (100 mL)
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent evaporated to constant weight

Sources & evidence

ORD record
ord-95adbdb97d5141afbc128e0b5f72809b
Source dataset
uspto-grants-2015_03
Patent number
US08987254B2

Reaction notes

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