N-Methylcyclohexylamine → HCID 52438095, compound

HRID 2388095Notes

Reaction equation

HRID 2388095 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CN1CCCC1=O.F[C:23]1[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=1[N+:30]([O-:32])=[O:31]>O>[CH:9]1([N:8]([CH3:7])[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][C:24]=2[N+:30]([O-:32])=[O:31])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 7514N-MethylcyclohexylamineHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 677672,5-Difluoronitrobenzene

Product 1

HCID 52438095HCID 52438095, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (6.0 g, 43.5 mmol) and N-methylcyclohexylamine (4.6 g, 40.6 mmol) were added to a N-methylpyrolidone (NMP) solution (20 ml) of 2,5-difluoronitrobenzene (5.0 g, 31.4 mmol), and stirred at 100° C. for 3 hours. The reaction mixture was cooled to room temperature, water was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and then dried over anhydrous magnesium sulfate. The resulting dry product was concentrated under reduced pressure to thereby obtain 7.0 g of oily yellow N-cyclohexyl-4-fluoro-2-nitro-N-methylaniline (yield: 89%).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationThe resulting dry product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a883b517627c45aeb6c52084293237b3
Source dataset
uspto-grants-2012_09
Patent number
US08269011B2

Reaction notes

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