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

HRID 10778

Reaction equation

HRID 10778 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-994cbfeb630d41b6b2862208213baf98
Source dataset
uspto-grants-2006_08
Patent number
US07094896B2

Linked notes

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