Water → HCID 22380652, compound

HRID 895634Notes

Reaction equation

HRID 895634 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:24])[CH2:10][CH2:9]1)C1C=CC=CC=1.Cl[C:26]([O:28][CH2:29][CH3:30])=[O:27].C(=O)([O-])O.[K+].O>ClCCl>[CH2:29]([O:28][C:26]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[C:20]([N+:21]([O-:23])=[O:22])=[CH:19][CH:18]=[CH:17][C:16]=2[CH3:24])[CH2:10][CH2:9]1)=[O:27])[CH3:30]

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 516893Potassium BicarbonateHCID 22380702HCID 22380702, compound

Product 1

HCID 22380652HCID 22380652, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-4-[(2-methyl-6-nitrophenyl)amino]piperidine (45.2 mg) was dissolved in dichloromethane (0.9 ml), added with ethyl chloroformate (27 μl) and potassium hydrogencarbonate (28 mg) and stirred at room temperature for 30 minutes. The reaction mixture was added with water (2 ml) and extracted twice with ethyl acetate (2 ml). The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1) to obtain 38.3 mg of the title compound. Yield: 90%.

Workup

  1. extractionextracted twice with ethyl acetate (2 ml)
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by preparative thin layer silica gel column chromatography (developing solvent: hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-393efe1d2a624b6f9feafb6ee76dbd6f
Source dataset
uspto-grants-2005_07
Patent number
US06916822B2

Reaction notes

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