Ethanolamine → N-(2-Hydroxyethyl)-2-(isopropyl)-5-methylcyclohexanecarboxamide

HRID 26386Notes

Reaction equation

HRID 26386 reaction equation
[CH:1]1([CH3:13])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([C:10](Cl)=[O:11])[CH2:2]1.[CH2:14]([CH2:16][NH2:17])[OH:15]>C(Cl)(Cl)Cl>[OH:15][CH2:14][CH2:16][NH:17][C:10]([CH:3]1[CH:4]([CH:7]([CH3:9])[CH3:8])[CH2:5][CH2:6][CH:1]([CH3:13])[CH2:2]1)=[O:11]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 3016102N-(2-Hydroxyethyl)-2-(isopropyl)-5-methylcyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of p-menth-3-oyl chloride prepared as in Example 1 (4.0g., 0.020 moles) in chloroform (30 ml.) was added dropwise to a stirred solution of ethanolamine (3 g., 0.043 moles) in chloroform (50 ml.). The reaction mixture becomes warm, goes cloudy and finally a yellow oil starts to separate out. After stirring for 2 hours at room temperature the mixture was poured into water. The organic layer was separated, washed with dilute H2SO4, and dried (MgSO4). Removal of the solvent left a viscous oil (3.8 g.). This was distilled under vacuum to yield N-(2-hydroxyethyl)-p-menthane-3-carboxamide as a colourless very viscous oil, b.p. 160°/01. mm.

Workup

  1. temperatureThe reaction mixture becomes warm
  2. customfinally a yellow oil starts to separate out
  3. additionwas poured into water
  4. customThe organic layer was separated
  5. washwashed with dilute H2SO4
  6. dry with materialdried (MgSO4)
  7. customRemoval of the solvent
  8. waitleft a viscous oil (3.8 g.)
  9. distillationThis was distilled under vacuum

Sources & evidence

ORD record
ord-d4a83106185d4c60b359d7037c4b05d9
Source dataset
uspto-grants-1979_04
Patent number
US04150052

Reaction notes

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