Acetyl chloride → HCID 86662022, compound

HRID 591647Notes

Reaction equation

HRID 591647 reaction equation
[CH3:1][CH:2]1[NH:7][CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:3]1.CCN(CC)CC.[C:23](Cl)(=[O:25])[CH3:24]>C(Cl)Cl>[C:23]([N:7]1[CH2:6][CH2:5][N:4]([C:8]2[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][CH:9]=2)[CH2:3][CH:2]1[CH3:1])(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86662021HCID 86662021, compound

Product 1

HCID 86662022HCID 86662022, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-(3-methylpiperazin-1-yl)benzaldehyde (1.0 g, 4.89 mmol) in methylene chloride (15 mL) was cooled to 0° C. and treated with Et3N (0.68 mL, 4.89 mmol), followed by acetyl chloride (0.34 mL, 4.89 mmol). The resulting solution was stirred at 0° C. for 20 minutes and then concentrated in vacuo. The material was purified by flash chromatography on silica gel, eluting with 0% to 5% of EtOAc/CH2Cl2, to afford 4-(4-acetyl-3-methylpiperazin-1-yl)benzaldehyde (0.88 g, 73%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe material was purified by flash chromatography on silica gel
  3. washeluting with 0% to 5% of EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-3dddde0ba647423db20a8e6bbdeba949
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

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