N-Methylcyclohexylamine → HCID 13251324, compound

HRID 905123Notes

Reaction equation

HRID 905123 reaction equation
Br[CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].C(N(CC)CC)C.[CH:20]1([NH:26][CH3:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1>C1(C)C=CC=CC=1>[CH:20]1([N:26]([CH:2]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:27])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

5

Reactant 3

HCID 7514N-MethylcyclohexylamineHCID 8471TriethylamineHCID 69637Diethyl bromomalonate

Product 1

HCID 13251324HCID 13251324, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Diethyl bromomalonate (17.0 g), triethylamine (9.1 g), and dry toluene (10 ml) were mixed, and with stirring, the mixture was heated under reflux. Then, N-cyclohexyl-N-methylamine (8.1 g) diluted with dry toluene (5 ml) was added dropwise, and the mixture was heated under reflux for 2.5 hours with stirring. The reaction mixture was washed with water three times, and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was distilled under reduced pressure to give 5.5 g (29%) of diethyl (N-cyclohexyl-N-methylamino)malonate having the following properties.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. additionwas added dropwise
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for 2.5 hours
  6. stirringwith stirring
  7. washThe reaction mixture was washed with water three times
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure
  10. distillationThe residue was distilled under reduced pressure

Sources & evidence

ORD record
ord-9b9e3a5f0b544e96af9f9edfbef1e2c1
Source dataset
uspto-grants-1983_12
Patent number
US04421914

Reaction notes

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