1-Benzylpiperazine → HCID 67806111, compound

HRID 1647884Notes

Reaction equation

HRID 1647884 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11](Cl)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)([OH:3])=[O:2].[CH2:19]([N:26]1[CH2:31][CH2:30][N:29]([CH2:32][CH2:33][NH2:34])[CH2:28][CH2:27]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N1CCNCC1)C1C=CC=CC=1.Br.BrCCN.CC(C)([O-])C.[K+]>C(O)C.O.C(N(CC)CC)C>[C:1]([CH2:4][CH2:5][NH:6][C:7](=[O:18])[C:8]1[CH:13]=[CH:12][C:11]([NH:34][CH2:33][CH2:32][N:29]2[CH2:30][CH2:31][N:26]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:27][CH2:28]2)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=1)([OH:3])=[O:2]

Participants

9

Reactant 5

HCID 759941-BenzylpiperazineHCID 27353312-(4-Benzylpiperazin-1-yl)ethan-1-amineHCID 27742172-Bromoethylamine hydrobromideHCID 23665647Potassium tert-butoxideHCID 60657227HCID 60657227, compound

Product 1

HCID 67806111HCID 67806111, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

8.2 g of 4-chloro-3-nitro-benzoic acid-[N-(2-carboxy-ethyl)-amide](prepared from 4-chloro-3-nitro-benzoylchloride and β-alanine-methylester and subsequent saponification with 48% hydrobromic acid), 6.6 g of 2-(4-benzyl-piperazino)-ethylamine (prepared from 1-benzyl-piperazine and 2-bromo-ethylamine-hydrobromide in ethanol with the addition of potassium tert.butoxide), 4.2 ml of triethylamine and 25 ml of water are heated over a steam bath for 8 hours. The mixture is evaporated down and purified by column chromatography (silica gel; methylene chloride/methanol/glacial acetic acid=8:2:0.1 to 2:1:0.1). Yield: 9.2 g (67% of theory), Rf value: 0.47 (silica gel; methylene chloride/methanol/conc. ammonia=8:2:0.1)

Workup

  1. temperatureare heated over a steam bath for 8 hours
  2. customThe mixture is evaporated down
  3. custompurified by column chromatography (silica gel; methylene chloride/methanol/glacial acetic acid=8:2:0.1 to 2:1:0.1)

Sources & evidence

ORD record
ord-e2d652484b2e46299f0ffd3fb44fc75f
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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