Methyl Isocyanate → HCID 53728120, compound

HRID 616544Notes

Reaction equation

HRID 616544 reaction equation
[CH2:1]([C:3]1([CH3:14])[CH:8]([CH3:9])[CH:7]([OH:10])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4]1)[CH3:2].[CH3:15][N:16]=[C:17]=[O:18]>C1(C)C(C)=CC=CC=1>[CH3:15][NH:16][C:17](=[O:18])[O:10][CH:7]1[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[NH:4][C:3]([CH2:1][CH3:2])([CH3:14])[CH:8]1[CH3:9]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 221822412,6-Diethyl-2,3,6-trimethylpiperidin-4-ol2×

Product 1

HCID 53728120HCID 53728120, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

4.0 g of 2,6-diethyl-2,3,6-trimethyl-4-piperidinol (Compound 1) and 1.7 g of methyl isocyanate were dissolved in 6 ml of xylene and the solution was refluxed by heating for 3.5 hours. Xylene and excess methyl isocyanate were distilled off under reduced pressure. The residue was purified by column chromatography on silica gel ("60F 254", available from Merck & Co.) using a 4 : 1 by volume mixture of chloroform and methanol as eluent. The product was then distilled under reduced pressure, giving 5.0 g of Compound 66 as a pale yellow liquid (bp 145° - 149° C/1.4 mmHg).

Workup

  1. temperaturethe solution was refluxed
  2. temperatureby heating for 3.5 hours
  3. distillationXylene and excess methyl isocyanate were distilled off under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel ("60F 254", available from Merck & Co.)
  5. additionby volume mixture of chloroform and methanol as eluent
  6. distillationThe product was then distilled under reduced pressure

Sources & evidence

ORD record
ord-2ac982029cfd483186dcdc3096af9b37
Source dataset
uspto-grants-1978_02
Patent number
US04075165

Reaction notes

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