Water → 1-(4-Bromophenyl)-4-(diethylamino)butan-1-one

HRID 70571Notes

Reaction equation

HRID 70571 reaction equation
C(NCC)C.[CH2:6]([N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:25])[CH2:21]CCCl)=[CH:16][CH:15]=1.O>C(#N)C>[Br:13][C:14]1[CH:19]=[CH:18][C:17]([C:20](=[O:25])[CH2:21][CH2:7][CH2:6][N:8]([CH2:11][CH3:12])[CH2:9][CH3:10])=[CH:16][CH:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8021DiethylamineHCID 8471TriethylamineHCID 783174'-Bromo-4-chlorobutyrophenone

Product 1

HCID 128598381-(4-Bromophenyl)-4-(diethylamino)butan-1-oneYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

Diethylamine (180 mL) and triethylamine (90 mL) were added to a solution of 4′-bromo-4-chlorobutyrophenone (18.13 g) in acetonitrile (90 mL), and the mixture was stirred at 100° C. for one hour. The reaction solution was cooled to room temperature and water was added, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→ethyl acetate:methanol:triethylamine=40:4:1) to give 1-(4-bromophenyl)-4-(diethylamino)butan-1-one as a brown oil (9.02 g, 44%).

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was then evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1→ethyl acetate:methanol:triethylamine=40:4:1)

Sources & evidence

ORD record
ord-25dba8fe4ef64e2aa82acbaf62b79f06
Source dataset
uspto-grants-2014_09
Patent number
US08822503B2

Reaction notes

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