Acetyl chloride → 4-(4-Acetyl-3,5-dimethylpiperazin-1-yl)benzaldehyde

HRID 591643Notes

Reaction equation

HRID 591643 reaction equation
[CH3:1][CH:2]1[NH:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH2:3]1.CCN(CC)CC.[C:24](Cl)(=[O:26])[CH3:25]>C(Cl)Cl>[C:24]([N:7]1[CH:2]([CH3:1])[CH2:3][N:4]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH2:5][CH:6]1[CH3:8])(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 866620204-(3,5-Dimethylpiperazin-1-yl)benzaldehyde

Product 1

HCID 866620144-(4-Acetyl-3,5-dimethylpiperazin-1-yl)benzaldehydeYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3,5-dimethylpiperazin-1-yl)benzaldehyde (1.0 g, 4.6 mmol.) in CH2Cl2 (15 mL) was cooled to 0° C. and treated with Et3N (0.64 mL, 4.6 mmol) followed by acetyl chloride (0.33 mL, 4.6 mmol). The reaction stirred for 30 minutes, then concentrated in vacuo. Purification by flash chromatography on silica gel, eluting with 0% to 50% EtOAc/CH2Cl2, afforded 4-(4-acetyl-3,5-dimethylpiperazin-1-yl)benzaldehyde (1.0 g, 83%).

Workup

  1. concentrationconcentrated in vacuo
  2. customPurification by flash chromatography on silica gel
  3. washeluting with 0% to 50% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-8aab3bd97e3c4644856e4e4ab86b9e9c
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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