Ethyl bromoacetate → Ethyl (1,4-diazepan-1-yl)acetate

HRID 1894462Notes

Reaction equation

HRID 1894462 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1>CN(C)C=O>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][N:8]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)[CH3:7]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 68163Hexahydro-1,4-diazepine

Product 1

HCID 13057080Ethyl (1,4-diazepan-1-yl)acetateYield 13.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl bromoacetate (3.7 g, 18.4 mmol, Aldrich) was added in portions to a solution of homopiperazine (2.76 g, 27.6 mmol, Avocado) in N,N-dimethylformamide (15 mL) at room temperature over 1.5 h. The mixture was then stirred for additional 4 h followed by an aqueous workup. The crude was purified by column flash chromatography to give homopiperazine-acetic acid ethyl ester (471 mg).

Workup

  1. customThe crude was purified by column flash chromatography

Sources & evidence

ORD record
ord-b44dab3127274691bcf0e0d6d1dc58f8
Source dataset
uspto-grants-2013_08
Patent number
US08513239B2

Reaction notes

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