Formaldehyde → N-methyl-N-(3,5-dimethylcyclohexyl)-N-(4-nitrobenzyl)amine

HRID 1387910Notes

Reaction equation

HRID 1387910 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].[CH3:13][CH:14]1[CH2:19][CH:18]([CH3:20])[CH2:17][C:16](=O)[CH2:15]1.[CH2:22](N(CC)CC)C.C=O>ClCCCl>[CH3:22][N:10]([CH:16]1[CH2:15][CH:14]([CH3:13])[CH2:19][CH:18]([CH3:20])[CH2:17]1)[CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 1375443,5-DimethylcyclohexanoneHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 18472422N-methyl-N-(3,5-dimethylcyclohexyl)-N-(4-nitrobenzyl)amine

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In 1,2-dichloroethane (70 ml) were suspended p-nitro-benzylamine hydrochloride (3.8 g), 3,5-dimethylcyclo-hexanone (2.5 g) and triethylamine (2.8 ml). Under ice-cooling, to the mixture was added sodium triacetoxy boron hydride (5.9 g). Under nitrogen atmosphere, the mixture was stirred at room temperature over night. Under ice-cooling, to the mixture were added 37% formalin(1.8 ml) and sodium triacetoxy boron hydride (5.9 g). Under nitrogen atmosphere, the mixture was stirred at room temperature over night. The solvent was evaporated, and the residue was neutralized with sodium hydroxide. The mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, and dried with anhydrous magnesium sulfate. Under reduced pressure, the solvent was evaporated, and the residue was purified with silica gel column (ethyl acetate/hexane) to give 3 isomers of N-methyl-N-(3,5-dimethylcyclohexyl)-N-(4-nitrobenzyl)amine (4.3 g; (31-a), 0.7 g; (31-b), 0.2 g; (31-c)) as each yellow oil.

Workup

  1. temperatureUnder ice-cooling, to the mixture
  2. temperatureUnder ice-cooling, to the mixture
  3. stirringUnder nitrogen atmosphere, the mixture was stirred at room temperature over night
  4. customThe solvent was evaporated
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated sodium chloride solution
  7. dry with materialdried with anhydrous magnesium sulfate
  8. customUnder reduced pressure, the solvent was evaporated
  9. customthe residue was purified with silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bd8459dc774a4b799c52181b9af0707b
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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