Ethylene Oxide → 2,6-Diethyl-1-(2-hydroxyethyl)-2,3,6-trimethyl-4-piperidyl methylcarbamate

HRID 616549Notes

Reaction equation

HRID 616549 reaction equation
[CH3:1][NH:2][C:3](=[O:18])[O:4][CH:5]1[CH2:10][C:9]([CH2:12][CH3:13])([CH3:11])[NH:8][C:7]([CH2:15][CH3:16])([CH3:14])[CH:6]1[CH3:17].[CH2:19]1[O:21][CH2:20]1>CO.Cl>[CH3:1][NH:2][C:3](=[O:18])[O:4][CH:5]1[CH2:10][C:9]([CH2:12][CH3:13])([CH3:11])[N:8]([CH2:19][CH2:20][OH:21])[C:7]([CH2:15][CH3:16])([CH3:14])[CH:6]1[CH3:17]

Participants

5

Reactant 2

HCID 6354Ethylene OxideHCID 537281202,6-Diethyl-2,3,6-trimethyl-4-piperidyl methylcarbamate

Product 1

HCID 536336612,6-Diethyl-1-(2-hydroxyethyl)-2,3,6-trimethyl-4-piperidyl methylcarbamateYield 50.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 5.1 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidyl methylcarbamate (Compound 66 - prepared as described in Preparation 4) in 8 ml of methanol were added 1.74 g of ethylene oxide and 1 drop of concentrated hydrochloric acid. The mixture was heated overnight at 100° C in a sealed tube. When the reaction was complete, the reaction mixture was concentrated by evaporation under reduced pressure and the residue was purified by column chromatography on silica gel using a 1 : 1 by volume mixture of benzene and ethyl acetate as eluent, giving 3.0 g of Compound 84. The compound showed a single spot on thin layer chromatography on silica gel (developing solvent: benzene/ethyl acetate, 1 : 1 by volume), Rf value 0.51.

Workup

  1. concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography on silica gel using a 1 : 1
  3. additionby volume mixture of benzene and ethyl acetate as eluent

Sources & evidence

ORD record
ord-6fa19a7f9cb74d959f4b8bcd0de328ff
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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