Ethyl bromoacetate → 1-(2-Ethoxy-2-oxoethyl)-1-ethylpiperidin-1-ium bromide

HRID 1897535Notes

Reaction equation

HRID 1897535 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:2].[CH2:9]([O:11][C:12](=[O:15])[CH2:13][Br:14])[CH3:10]>ClCCl>[Br-:14].[CH2:9]([O:11][C:12](=[O:15])[CH2:13][N+:3]1([CH2:1][CH3:2])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1)[CH3:10]

Participants

4

Reactant 2

HCID 7748Ethyl bromoacetateHCID 13007N-Ethylpiperidine

Product 1

HCID 30482831-(2-Ethoxy-2-oxoethyl)-1-ethylpiperidin-1-ium bromideYield 98.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-ethylpiperidine (2.5 g, 22.1 mmol) in dichloromethane (4 mL) was added ethylbromoacetate (3.7 g, 22.1 mmol) via a syringe. The mixture was stirred at room temperature overnight. The resulting white precipitate was washed with hexane and ethylacetate to give 6.1 g, 98.6% yield of the product as a white solid. Positive mode ESI/MS: m/z=200.4 (M+, minus Br); confirmed by 1H NMR.

Workup

  1. washThe resulting white precipitate was washed with hexane and ethylacetate

Sources & evidence

ORD record
ord-b4686a9f058d409caf8bc5ca5987b92d
Source dataset
uspto-grants-2013_08
Patent number
US08519125B2

Reaction notes

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