1-Acetylpiperazine → 1-[4-[3-(Benzylamino)-4-nitrophenyl]piperazin-1-yl]ethanone

HRID 1966429Notes

Reaction equation

HRID 1966429 reaction equation
[CH2:1]([NH:8][C:9]1[CH:14]=[C:13](Br)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:19]1([C:25](=[O:27])[CH3:26])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1>CN1C(=O)CCC1.O>[CH2:1]([NH:8][C:9]1[CH:14]=[C:13]([N:22]2[CH2:23][CH2:24][N:19]([C:25](=[O:27])[CH3:26])[CH2:20][CH2:21]2)[CH:12]=[CH:11][C:10]=1[N+:16]([O-:18])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 837951-AcetylpiperazineHCID 24902978N-benzyl-5-bromo-2-nitroaniline

Product 1

HCID 29027181-[4-[3-(Benzylamino)-4-nitrophenyl]piperazin-1-yl]ethanoneYield 68.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-benzyl-5-bromo-2-nitrobenzenamine (100 mg, 0.32 mmol) and 1-(piperazin-1-yl)ethanone (83 mg, 0.65 mmol) in NMP (1 mL) was heated to 110° C. for 16 h, cooled then diluted with H2O (15 mL) and extracted with ethyl acetate (2×15 mL). The organics were washed with brine (8 mL), dried (Na2SO4) then filtered and concentrated in vacuo. The residue was subjected flash silica column chromatography (100% ethyl acetate) to furnish 1-(4-(3-(benzylamino)-4-nitrophenyl)piperazin-1-yl)ethanone (mg, 0.22 mmol) as a yellow solid (71 mg, 0.19 mmol) 61% yield. 1H NMR (500 MHz, DMSO-D6) d (ppm) 8.83 (m, 1H), 7.93 (d, J=9.5 Hz, 1H), 7.39 (m, 4H), 7.28 (m, 1H), 6.40 (dd, J=2.5 Hz, 10 Hz, 1H), 5.96 (d, J=2.5 Hz, 1H), 4.58 (d, J=6 Hz, 2H) 3.50-3.29 (m, 8H), 2.34 (s, 3H).+ESI HRMS (calcd for C19H22N4NaO3, M+Na) 377.1590, found 377.1584

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washThe organics were washed with brine (8 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationthen filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26bc5ae687684019961742effa0ccac6
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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