Piperazine → N-ethyl-4-(piperazin-1-yl)benzamide

HRID 69591Notes

Reaction equation

HRID 69591 reaction equation
[CH2:1]([NH:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)[CH3:2].[NH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>>[CH2:1]([NH:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][C:8]([N:13]2[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 4693101N-ethyl-4-fluorobenzamide

Product 1

HCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideYield 77%

Procedure

Using N-ethyl-4-fluorobenzamide in the general procedure for nucleophilic aromatic substitution reactions with piperazine, the title compound was obtained (77% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.10 (t, J=7.07 Hz, 3 H) 2.25 (br. s., 1 H) 2.76-2.86 (m, 4 H) 3.09-3.18 (m, 4H) 3.21-3.28 (m, 2 H) 6.90 (m, J=8.84 Hz, 2 H) 7.67-7.75 (m, 2 H) 8.11 (t, J=5.31 Hz, 1 H). ESI-MS: m/z 234.2 (M+H)+. mp=131.3-134.4° C.

Sources & evidence

ORD record
ord-58c49c44c11643dbb717aee78d1928f3
Source dataset
uspto-grants-2014_09
Patent number
US08822470B2

Reaction notes

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