Water → (4-(4-Nitro-3-(propylamino)phenyl)piperazin-1-yl)(phenyl)methanone

HRID 1966430Notes

Reaction equation

HRID 1966430 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:12]([O-:14])=[O:13])=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[CH:7]=1.[C:15]1([C:21]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.O>CN1C(=O)CCC1>[N+:12]([C:5]1[CH:4]=[CH:3][C:2]([N:26]2[CH2:27][CH2:28][N:23]([C:21]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[O:22])[CH2:24][CH2:25]2)=[CH:7][C:6]=1[NH:8][CH2:9][CH2:10][CH3:11])([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 962WaterHCID 7626541-BenzoylpiperazineHCID 584256215-bromo-2-nitro-N-propylbenzenamine

Product 1

HCID 58425662(4-(4-Nitro-3-(propylamino)phenyl)piperazin-1-yl)(phenyl)methanoneYield 213.7%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 5-bromo-2-nitro-N-propylbenzenamine (250 mg, 1.02 mmol) and phenyl(piperazin-1-yl)methanone (578 mg, 3.06 mmol) in NMP (2 mL) was heated to 110° C. for 16 h. The solution was cooled to room temperature to which was slowly added H2O (5 mL). The resulting yellow precipitate was filtered, washed with 2 mL of water, dried (high vacuum, 14 h) to furnish (4-(4-nitro-3-(propylamino)phenyl)piperazin-1-yl)(phenyl)methanone (520 mg, 2.18 mmol), 56% yield. 1H NMR (500 MHz, DMSO-D6) d (ppm) 8.83 (m, 1H), 7.93 (d, J=9.5 Hz, 1H), 7.50-7.45 (m, 5H), 6.41 (dd, J=2.5 Hz, 10 Hz, 1H), 6.00 (d, J=2.5 Hz, 1H), 3.72-3.40 (m, 8H), 3.29 (q, J=7 Hz, 2H), 1.66 (m, 2H), 0.96 (t, J=7 Hz, 3H).+ESI HRMS (calcd for C20H24N4NaO, M+Na) 391.1746. found 391.1741

Workup

  1. filtrationThe resulting yellow precipitate was filtered
  2. washwashed with 2 mL of water
  3. customdried (high vacuum, 14 h)

Sources & evidence

ORD record
ord-f679124cc0fa49ea8900c8cd0d362ff3
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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