Acetyl chloride → 1-Acetyl-4-(4-nitrophenyl)piperazine

HRID 2213883Notes

Reaction equation

HRID 2213883 reaction equation
C(=O)([O-])[O-].[K+].[K+].[C:7](Cl)(=[O:9])[CH3:8].[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:16][CH:15]=1)([O-:13])=[O:12]>ClCCl>[C:7]([N:23]1[CH2:24][CH2:25][N:20]([C:17]2[CH:16]=[CH:15][C:14]([N+:11]([O-:13])=[O:12])=[CH:19][CH:18]=2)[CH2:21][CH2:22]1)(=[O:9])[CH3:8]

Participants

5

Reactant 3

HCID 6367Acetyl chloride2×HCID 11430Potassium Carbonate2×HCID 804471-(4-Nitrophenyl)piperazine

Product 1

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazineYield 722.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Powdered potassium carbonate (276 mg, 2 mmol) and then acetyl chloride (0.14 mL, 2 mmol) were added to a solution of 1-(4-nitrophenyl) piperazine (2.1 g, 1 mmol) (Acros Organics) in dichloromethane (75 mL). The mixture was stirred at room temperature overnight and then further quantities of powdered potassium carbonate (500 mg, 3.6 mmol) and acetyl chloride (0.2 mL, 2.8 mmol) were added. The mixture was stirred at room temperature overnight, then it was filtered and the filter cake was washed with dichloromethane. The solvent was evaporated from the filtrate, and the residue was chromatographed (0–66% acetone/dichloromethane) to give 1-acetyl-4-(4-nitrophenyl)piperazine (1.8 g, 72%).

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. filtrationit was filtered
  3. washthe filter cake was washed with dichloromethane
  4. customThe solvent was evaporated from the filtrate
  5. customthe residue was chromatographed (0–66% acetone/dichloromethane)

Sources & evidence

ORD record
ord-423c854bb33c497e88387645e3edd072
Source dataset
uspto-grants-2006_09
Patent number
US07105670B2

Reaction notes

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