Ethanolamine → N-(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N'-(2-hydroxyethyl)oxamide

HRID 1975571Notes

Reaction equation

HRID 1975571 reaction equation
[CH:1]1([O:7][N:8]2[C:13]([CH3:15])([CH3:14])[CH2:12][CH:11]([NH:16][C:17](=[O:22])[C:18](OC)=[O:19])[CH2:10][C:9]2([CH3:24])[CH3:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:25]([CH2:27][NH2:28])[OH:26]>C1(C)C=CC=CC=1>[CH:1]1([O:7][N:8]2[C:13]([CH3:14])([CH3:15])[CH2:12][CH:11]([NH:16][C:17]([C:18]([NH:28][CH2:27][CH2:25][OH:26])=[O:19])=[O:22])[CH2:10][C:9]2([CH3:24])[CH3:23])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 700EthanolamineHCID 23372095methyl N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)oxamate

Product 1

HCID 23372097N-(1-Cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)-N'-(2-hydroxyethyl)oxamideYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 9.1 grams (26.7 mmol) of methyl N-(1-cyclohexyloxy-2,2,6,6-tetramethylpiperidin-4-yl)oxamate, 1.8 grams (29.4 mmol) of ethanolamine and 35 ml of toluene is heated at reflux for 30 minutes. Methanol is removed from the reaction mixture by fractional distillation. The reaction mixture is poured into ethyl acetate (125 ml) to afford 6.3 grams (64% yield) of the title compound as a white solid melting at 190°-1920° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 30 minutes
  3. customMethanol is removed from the reaction mixture by fractional distillation
  4. additionThe reaction mixture is poured into ethyl acetate (125 ml)

Sources & evidence

ORD record
ord-c045bf77f79c45a2baae3f20db4701bc
Source dataset
uspto-grants-1994_02
Patent number
US05286865

Reaction notes

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