Diethanolamine → N,N-Bis(2-hydroxyethyl)-p-menthane-3-carboxamide

HRID 26387Notes

Reaction equation

HRID 26387 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.[NH:14]([CH2:18][CH2:19][OH:20])[CH2:15][CH2:16][OH:17]>C(Cl)(Cl)Cl>[OH:17][CH2:16][CH2:15][N:14]([CH2:18][CH2:19][OH:20])[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 8113DiethanolamineHCID 13734319Cyclohexanecarbonyl chloride, 5-methyl-2-(1-methylethyl)-

Product 1

HCID 23338130N,N-Bis(2-hydroxyethyl)-p-menthane-3-carboxamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of p-menth-3-oyl chloride (4.0 g., 0.020 moles) in chloroform (30 ml.) was added dropwise to a stirred solution of diethanolamine (4.2 g., 0.044 moles) in chloroform (50 ml.). The reaction mixture goes cloudy and a yellow oil separates out. After 2 hours at room temperature, the yellow oil (upper layer) was separated. Infra red spectographic analysis indicated this to be (HOCH2CH2)2NH2+Cl-. Removal of the chloroform left a viscous oil (6 g.). Thin layer chromatography (CHCl3 and CHCl3 +10% CH3OH) indicated it to consist of one major component and a minor component of larger Rf value. This was separated by column chromatography on neutral alumina (activity 1). Eluting with chloroform (200 ml.) removed the minor component and the major product was eluted from the column with chloroform+5% methanol. The major component was shown to be N,N-bis(2-hydroxyethyl)-p-menthane-3-carboxamide.

Workup

  1. customthe yellow oil (upper layer) was separated
  2. customRemoval of the chloroform
  3. waitleft a viscous oil (6 g.)
  4. customThis was separated by column chromatography on neutral alumina (activity 1)
  5. washEluting with chloroform (200 ml.)
  6. customremoved the minor component
  7. washthe major product was eluted from the column with chloroform+5% methanol

Sources & evidence

ORD record
ord-66d92c5dddf94cb889ca28fc8b939fb8
Source dataset
uspto-grants-1979_04
Patent number
US04150052

Reaction notes

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