Potassium Carbonate → 4-(4-Acetylpiperazin-1-yl)benzaldehyde

HRID 1505608Notes

Reaction equation

HRID 1505608 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[N:16]1([C:22](=[O:24])[CH3:23])[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1>CN(C)C=O.CCOC(C)=O>[C:22]([N:16]1[CH2:21][CH2:20][N:19]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:18][CH2:17]1)(=[O:24])[CH3:23]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 680234-FluorobenzaldehydeHCID 837951-Acetylpiperazine

Product 1

HCID 20521464-(4-Acetylpiperazin-1-yl)benzaldehydeYield 64%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of 4-fluorobenzaldehyde (5 g, 40.2 mmol) in N,N-dimethylformamide (130 mL) was added potassium carbonate (8.35 g, 60.4 mmol) and 1-piperazin-1-ylethanone (10.3 g, 80.5 mmol) and the reaction was stirred at 130° C. for 16 hours. The reaction was then cooled to ambient temperature, diluted with EtOAc and washed with water (×2) and brine. The organic layer was then dried with MgSO4, concentrated and purified by silica gel column chromatography (0-10% methanol in dichloromethane) to give 4-(4-acetylpiperazin-1-yl)benzaldehyde (5.96 g, 64% yield). LCMS (m/z) ES+ 233 [M+1]+.

Workup

  1. temperatureThe reaction was then cooled to ambient temperature
  2. washwashed with water (×2) and brine
  3. dry with materialThe organic layer was then dried with MgSO4
  4. concentrationconcentrated
  5. custompurified by silica gel column chromatography (0-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-41557fbca4704720bb353daa05f19906
Source dataset
uspto-grants-2015_12
Patent number
US09216988B2

Reaction notes

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