Triethanolamine → N-Cyclohexyl-4,4-dimethyl-3-oxopentanamide

HRID 1730617Notes

Reaction equation

HRID 1730617 reaction equation
C(O[C:4](=[O:12])[CH2:5][C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8])C.[CH:13]1([NH2:19])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.N(CCO)(CCO)CCO>C1(C)C=CC=CC=1>[CH:13]1([NH:19][C:4](=[O:12])[CH2:5][C:6](=[O:11])[C:7]([CH3:8])([CH3:9])[CH3:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

5

Reactant 3

HCID 7618TriethanolamineHCID 7965CyclohexylamineHCID 86950Ethyl pivaloylacetate

Product 1

HCID 13738452N-Cyclohexyl-4,4-dimethyl-3-oxopentanamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethylpivaloylacetate (172 g.), cyclohexylamine (99 g.), triethanolamine (1 g.) and toluene (200 ml.) are mixed in a distillation flask and heated at reflux under a 6 in. Vigreux distillation column. When the head temperature stabilized at 82° C. distillation was begun at a take off to reflux ratio of 1 to 10. Distillation was continued until a head temperature of 110° C. is obtained. The remainder of the solvent is removed in a vacuum and residue is crystallized by trituation with hexane. A yield of 201 g. of product melting at 69°-70° C. is obtained.

Workup

  1. temperatureheated
  2. temperatureat reflux under a 6 in
  3. distillationVigreux distillation column
  4. customstabilized at 82° C.
  5. distillationdistillation
  6. temperatureto reflux ratio of 1 to 10
  7. distillationDistillation
  8. customwas continued until a head temperature of 110° C.
  9. customis obtained
  10. customThe remainder of the solvent is removed in a vacuum and residue
  11. customis crystallized by trituation with hexane

Sources & evidence

ORD record
ord-2fa57a9388fe408f88b73c7e6cd0cb96
Source dataset
uspto-grants-1976_11
Patent number
US03993637

Reaction notes

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