Benzyl Bromide → HCID 46198774, compound

HRID 1966470Notes

Reaction equation

HRID 1966470 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:16]=[CH:17][C:18]([N+:28]([O-:30])=[O:29])=[C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:20]=2)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH2:31]([N:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:19]1[CH:20]=[C:15]([N:12]2[CH2:11][CH2:10][N:9]([C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:14][CH2:13]2)[CH:16]=[CH:17][C:18]=1[N+:28]([O-:30])=[O:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 44814403HCID 44814403, compound

Product 1

HCID 46198774HCID 46198774, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 1140TolueneSolvent

Procedure

A suspension of 5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (1.0 g, 2.5 mmol), benzylbromide (0.3 ml, 2.5 mmol), potassium hydroxide (0.18 g, 3.2 mmol) and tetra-butyl ammonium iodide (0.05 g, 0.25 mmol) in 40 ml toluene was stirred at room temperature overnight. The red solids were filtered to get N-benzyl-5-(4-benzoylpiperazin-1-yl)-2-nitro-N-phenylbenzenamine (1.1 g, 90%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 3.40-3.58 (m, br, 8H), 4.94 (s, 2H), 6.30 (d, J=8.0 Hz, 2H), 6.73 (t, J=7.2 Hz, 1H), 6.88 (d, J=9.2 Hz, 2H), 7.09-7.48 (m, 12H), 7.98 (d, J=8.9 Hz, 1H).

Workup

  1. filtrationThe red solids were filtered

Sources & evidence

ORD record
ord-3831fd5349ef4df0a8394682f1676da3
Source dataset
uspto-grants-2013_04
Patent number
US08420640B2

Reaction notes

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