Ethylene Oxide → N-n-butyl-N-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-yl]acetamide

HRID 1955967Notes

Reaction equation

HRID 1955967 reaction equation
[CH2:1]([N:5]([CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[NH:12][C:11]([CH3:18])([CH3:17])[CH2:10]1)[C:6](=[O:8])[CH3:7])[CH2:2][CH2:3][CH3:4].[CH2:19]1[O:21][CH2:20]1.C(OCC)(=O)C.C(O)C.C(N(CC)CC)C>O.C(O)C>[CH2:1]([N:5]([CH:9]1[CH2:14][C:13]([CH3:16])([CH3:15])[N:12]([CH2:19][CH2:20][OH:21])[C:11]([CH3:17])([CH3:18])[CH2:10]1)[C:6](=[O:8])[CH3:7])[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6354Ethylene OxideHCID 212252644-(N-butylacetamido)-2,2,6,6-tetramethylpiperidineHCID 22328969EtOH ethyl acetate triethylamine

Product 1

HCID 19073314N-n-butyl-N-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-yl]acetamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

In general accordance with the procedure of Example 2Ag2, 27.2 g of crude product are obtained starting from 25.4 g (0.10 mol) of N-n-butyl-N-(2,2,6,6-tetramethyl-4-piperidinyl)acetamide [Example 2Ah1] and 17.6 g (0.40 mol) of ethylene oxide in 100 ml of water and 100 ml of ethanol. Chromatography over silica gel using the solvent system ethyl acetate/ethanol/triethylamine =30: 1:1 gives 17.2 (58%) of the desired N-n-butyl-N-[1-(2-hydroxyethyl)-2,2,6,6-tetramethylpiperidin-4-yl]acetamide in the form of a viscous oil which solidifies during storage; m.p. 72°-82° C.

Sources & evidence

ORD record
ord-bfd48b61ff8e475b90bc986518fad151
Source dataset
uspto-grants-1998_07
Patent number
US05777113

Reaction notes

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