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

HRID 505915Notes

Reaction equation

HRID 505915 reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH3:10][N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][N:11]1[CH2:16][CH2:15][N:14]([C:2]2[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 680234-Fluorobenzaldehyde

Product 1

HCID 7365334-(4-Methylpiperazin-1-yl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

20 g (161 mmol) of 4-fluorobenzaldehyde, 48.4 g (483 mmol) of 1-methylpiperazine and 22.3 g (161 mmol) of potassium carbonate were added to 50 ml of dimethylformamide, and the mixture was heated at 130° C. for 36 hours. The mixture was subsequently concentrated under reduced pressure. The residue was partitioned between ethyl acetate and 2 M hydrochloric acid. The aqueous phase was separated off and made alkaline using aqueous sodium bicarbonate solution. This aqueous phase was extracted with ethyl acetate, and the organic phase was separated off, dried and concentrated under reduced pressure. This gave 48.7 g of the intermediate.

Workup

  1. concentrationThe mixture was subsequently concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 2 M hydrochloric acid
  3. customThe aqueous phase was separated off
  4. extractionThis aqueous phase was extracted with ethyl acetate
  5. customthe organic phase was separated off
  6. customdried
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f1afe91be97a4424a45414f4d3d87b34
Source dataset
uspto-grants-2010_08
Patent number
US07781596B1

Reaction notes

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