Water → HCID 57555222, compound

HRID 220816Notes

Reaction equation

HRID 220816 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH3:8].[CH:9]1([NH:15][C:16]2[C:17]([NH2:22])=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.O>CN(C=O)C>[CH:9]1([NH:15][C:16]2[C:17]([NH:22][CH3:8])=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1517328N~1~-Cyclohexylbenzene-1,2-diamine

Product 1

HCID 57555222HCID 57555222, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Potassium carbonate (2.45 g, 17.7 mmol) and iodomethane (0.81 ml, 13.0 mmol) were added to a solution of N-cyclohexyl-benzene-1,2-diamine from Example E26.2 (2.25 g, 11.8 mmol) in DMF (10 ml). The mixture was stirred for 6 h at room temperature then poured into water and extracted with EtOAc. The organic layer was washed with water then brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 5% EtOAc:95% hexane) to yield the title compound (950 mg, 39%).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with water
  3. dry with materialbrine, dried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 5% EtOAc:95% hexane)

Sources & evidence

ORD record
ord-c29c950c60ad4e6287372633c148642e
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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