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

HRID 1756851Notes

Reaction equation

HRID 1756851 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°-192° 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-5a12b31d27a94d9ea2676ead05646264
Source dataset
uspto-grants-1995_08
Patent number
US05442071

Reaction notes

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