Glycidol → N-{2-[(2,3-Dihydroxypropyl)amino]ethyl}-2-methylpropanamide

HRID 2291891Notes

Reaction equation

HRID 2291891 reaction equation
[CH:1]([C:4]([NH:6][CH2:7][CH2:8][NH2:9])=[O:5])([CH3:3])[CH3:2].[CH2:10]1[O:12][CH:11]1[CH2:13][OH:14]>C(O)(C)C>[CH3:2][CH:1]([C:4]([NH:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:12])[CH2:13][OH:14])=[O:5])[CH3:3]

Participants

4

Reactant 2

HCID 11164GlycidolHCID 12681828N-(2-Aminoethyl)-2-methylpropanamide

Product 1

HCID 14347794N-{2-[(2,3-Dihydroxypropyl)amino]ethyl}-2-methylpropanamideYield 30.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
25 °C

Procedure

To 39 g (0.3 mol) of 2-(isopropylcarbonylamino)ethylamine in 150 ml of isopropyl alcohol was added 22.2 g (0.3 mol) of glycidol. The reaction mixture was stirred at 25° C. for 24 hours and evaporated in vacuo. The residual oil was chromatographed (silica gel/ethanol) to give 18.6 g (30%) of product. This compound was identified by NMR and IR spectroscopy.

Workup

  1. customevaporated in vacuo
  2. customThe residual oil was chromatographed (silica gel/ethanol)

Sources & evidence

ORD record
ord-07a5554ace9e48c3a597903e807acac0
Source dataset
uspto-grants-1989_01
Patent number
US04798892

Reaction notes

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