Acetic Anhydride → 1-(4-(3-Methoxy-4-nitrophenyl)piperazin-1-yl)ethanone

HRID 1014210Notes

Reaction equation

HRID 1014210 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].C(N(CC)CC)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>ClCCl>[C:25]([N:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:14]1)(=[O:27])[CH3:26]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 39674091-(3-Methoxy-4-nitrophenyl)piperazine

Product 1

HCID 594418231-(4-(3-Methoxy-4-nitrophenyl)piperazin-1-yl)ethanoneYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[3-(methyloxy)-4-nitrophenyl]piperazine (0.5 g, 2.11 mmol) and triethylamine (1.27 g, 12.63 mmol, Aldrich) in dichloromethane (25 mL) was added acetic anhydride (0.64 g, 6.35 mmol, Aldrich). After stirring 3 hrs at rt, the reaction was washed with water (25 mL), organic layer adsorbed to silica gel and purified by column chromatography (dichloromethane to 10% methanol/dichloromethane) to give 1-acetyl-4-[3-(methyloxy)-4-nitrophenyl]piperazine (0.4 g, 68%). ESIMS (M+H)+=280.

Workup

  1. washthe reaction was washed with water (25 mL), organic layer
  2. custompurified by column chromatography (dichloromethane to 10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-374361a6b31346c0afc1b3a287b3180f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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