Water → HCID 44814403, compound

HRID 1966431Notes

Reaction equation

HRID 1966431 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:15]([O-:17])=[O:16])=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:7]=1.[C:18]1([C:24]([N:26]2[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN1C(=O)CCC1>[N+:15]([C:5]1[CH:4]=[CH:3][C:2]([N:29]2[CH2:30][CH2:31][N:26]([C:24]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:25])[CH2:27][CH2:28]2)=[CH:7][C:6]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([O-:17])=[O:16]

Participants

5

Reactant 3

HCID 962WaterHCID 2386965-bromo-2-nitro-n-phenylanilineHCID 7626541-Benzoylpiperazine

Product 1

HCID 44814403HCID 44814403, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of N-(5-bromo-2-nitrophenyl)benzenamine (200 mg, 0.68 mmol) and phenyl(piperazin-1-yl)methanone (257 mg, 1.36 mmol) in NMP (1.5 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-(phenylamino)phenyl)piperazin-1-yl)(phenyl)methanone (187 mg, 0.46 mmol), 68% yield. 1H NMR (500 MHz, CDCl3) d (ppm) 3.10-3.61 (m, 8H), 6.34 (dd, J=2.6, 9.7 Hz, 1H), 6.41 (d, J=2.6 Hz, 1H), 7.24-7.48 (m, 10H), 8.19 (d, J=9.7 Hz, 1H), 9.86 (s, 1H). 13C NMR (125 MHz, CDCl3): d (ppm) 171.0, 155.7, 145.8, 139.3, 135.5, 130.6, 130.2, 129.4, 129.1, 127.6, 126.1, 125.0, 106.2, 96.9, 46.7, 29.9.

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-f1b75caa315d465aad9908fe94121ec6
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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