Triethylamine → N1-(4-nitrobenzyl)-N4-phenacyl piperazine dihydrochloride

HRID 2055217Notes

Reaction equation

HRID 2055217 reaction equation
[ClH:1].Cl.[N+:3]([C:6]1[CH:18]=[CH:17][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4].C(N(CC)CC)C.[Cl:26][CH2:27][C:28]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:29]>C1C=CC=CC=1>[ClH:26].[ClH:1].[N+:3]([C:6]1[CH:18]=[CH:17][C:9]([CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH2:27][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:29])[CH2:13][CH2:12]2)=[CH:8][CH:7]=1)([O-:5])=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 107572-ChloroacetophenoneHCID 180056791-(4-Nitrobenzyl)piperazine dihydrochloride

Product 1

HCID 86606197N1-(4-nitrobenzyl)-N4-phenacyl piperazine dihydrochlorideYield 59.51%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of N-(4-nitrobenzyl)piperazine dihydrochloride (7.73 g, 30 mmol), triethylamine (8.37 ml, 60 mmol) and 2-chloro-1-phenylethanone (6.12 g, 39 mmol) in 100 ml of benzene was refluxed for 5 hours, and then treated according to general preparation 2 to give 5.2 g of compound (IV-4), yield 59.51%, mp 236-238° C. M+ 339.

Workup

  1. temperaturewas refluxed for 5 hours
  2. additiontreated
  3. customaccording to general preparation 2

Sources & evidence

ORD record
ord-3e33b0424ad041a4aa8e3eae9ec5f55f
Source dataset
uspto-grants-2008_02
Patent number
US07332495B2

Reaction notes

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