Methyl bromoacetate → methyl 2-[N-(2-cyclohex-1-enyl)ethylamino]acetate

HRID 23597Notes

Reaction equation

HRID 23597 reaction equation
Br[CH2:2][C:3]([O:5][CH3:6])=[O:4].[C:7]1([CH2:13][CH2:14][NH2:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=1>C(Cl)Cl>[CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][C:7]=1[CH2:13][CH2:14][NH:15][CH2:2][C:3]([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 60984Methyl bromoacetateHCID 769382-(1-Cyclohexenyl)ethylamine

Product 1

HCID 62326904methyl 2-[N-(2-cyclohex-1-enyl)ethylamino]acetateYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl bromoacetate (5 g, 32.7 mmol) in DCM (150 mL) was added 2-(1-cyclohexenyl)ethylamine (11.4 ml, 81.71 mmol) over 5 min. After 2 h, the solvent was removed and the residue purified on silica gel (Merck 60; (1:9) ethyl acetate/hexane) to afford methyl 2-[N-(2-cyclohex-1-enyl)ethylamino]acetate (5.0 g, 78%).

Workup

  1. customthe solvent was removed
  2. customthe residue purified on silica gel (Merck 60; (1:9) ethyl acetate/hexane)

Sources & evidence

ORD record
ord-2836cb80e50c435098e844f743189272
Source dataset
uspto-grants-2005_02
Patent number
US06852752B2

Reaction notes

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