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

HRID 2414489Notes

Reaction equation

HRID 2414489 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N([CH2:21][CH3:22])CC)C.C(=O)(O)[O-:24].[Na+]>ClCCl>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:21](=[O:24])[CH3:22])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 804471-(4-Nitrophenyl)piperazineHCID 516892Sodium Bicarbonate

Product 1

HCID 28651491-Acetyl-4-(4-nitrophenyl)piperazine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

1-(4-Nitrophenyl)piperazine (2.5 g, 12.1 mmol) was dissolved in dichloromethane (100 ml). Triethylamine (2.0 ml, 14.5 mmol) was added and the reaction was cooled to 0° C. Atetic anhydride (1.25 ml, 13.3 mmol) was added dropwise and the reaction was stirred at 0° C. for 1 h. Saturated sodium bicarbonate was added and the reaction was extracted (×3) with dichloromethane, dried (MgSO4), filtered and concentrated in vacuo to give 4-(4-nitrophenyl)-1-acetylpiperazine as a yellow solid (3.01 g). GC/MS (EI, M+) m/z=249.

Workup

  1. extractionthe reaction was extracted (×3) with dichloromethane
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc626c68efbb46a7acc269ae6921e340
Source dataset
uspto-grants-2004_11
Patent number
US06812225B2

Reaction notes

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