Benzene → Ethyl 1,4-dibenzylpiperazine-2-carboxylate

HRID 496036Notes

Reaction equation

HRID 496036 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][NH:10][CH2:9][CH2:8][NH:7]1)=[O:5])[CH3:2].[CH2:12](N(CC)CC)C.CO[C:21]1[CH:32]=[CH:31][CH:30]=[CH:29][C:22]=1[C:23](Br)(OC)OC.[CH:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][N:10]([CH2:23][C:22]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:21]=2)[CH2:9][CH2:8][N:7]1[CH2:12][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:5])[CH3:2]

Participants

5

Reactant 4

HCID 241Benzene2×HCID 8471TriethylamineHCID 10633257Ethyl Piperazine-2-carboxylateHCID 22324253Trimethoxy benzylbromide

Product 1

HCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateYield 44%

Procedure

Piperazine 2-carboxylic acid ethyl ester (2.25 g, 14.25 mmol) was dissolved in dry benzene (30 ml) followed by addition of triehylamine (2.2 ml, 15.67 mmol). Trimethoxybenzyl bromide (3.72 g, 14.25 mmol) in dry benzene (30 ml) was added dropwise. The resulting mixture was stirred under nitrogen at room temperature overnight. The resulting salt was removed through filtration and solvent was evaporated. The crude product was purified by column chromatography using CH2Cl2:MeOH (15:1) to give the desired product in 44% yield.

Workup

  1. customThe resulting salt was removed through filtration and solvent
  2. customwas evaporated
  3. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6ea125ead655430eb0acd8e294cd7f58
Source dataset
uspto-grants-2005_09
Patent number
US06943168B2

Reaction notes

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