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

HRID 903310Notes

Reaction equation

HRID 903310 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 (4.0 g., 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-4d0954d73fc345648aec9ed28939f9c4
Source dataset
uspto-grants-1980_10
Patent number
US04226988

Reaction notes

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