Benzylamine → N-Benzylglycine ethyl ester

HRID 1853384Notes

Reaction equation

HRID 1853384 reaction equation
C(N(C(C)C)CC)(C)C.[CH2:10]([NH2:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(OCC)(=O)C>O1CCOCC1>[CH2:10]([NH:17][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 7504BenzylamineHCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 81531Diisopropylethylamine

Product 1

HCID 80908N-Benzylglycine ethyl esterYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of diisopropylethylamine (155 g, 1.2 mol) and benzylamine (96 g, 0.9 mol) was added dropwise to a solution of ethyl bromoacetate (100 g, 0.6 mol) in dioxane (1000 mL). The resulting suspension was heated at about 90° C. for about 5 hours, and then was cooled to ambient temperature. Standard extractive workup with ethyl acetate afforded the title product as a yellow oil (90 g; yield=80%). LC-MS: m/z=194 (M+H)+.

Workup

  1. temperaturewas cooled to ambient temperature

Sources & evidence

ORD record
ord-45033250858e43b693d80f205fbca829
Source dataset
uspto-grants-2015_02
Patent number
US08962638B2

Reaction notes

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