N-Methylcyclohexylamine → HCID 52438095, compound

HRID 2167446Notes

Reaction equation

HRID 2167446 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-754f22ab82bb4169b5dee5d937b4b408
Source dataset
uspto-grants-2015_06
Patent number
US09045464B2

Reaction notes

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