2-Nitrophenyl isocyanate → 2-[1-(4-Pyridyl)piperidin-4-ylmethylaminocarbonyl]amino-nitrobenzene

HRID 2301848Notes

Reaction equation

HRID 2301848 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9][CH2:8]2)=[CH:3][CH:2]=1.[N+:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]=[C:25]=[O:26])([O-:17])=[O:16]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][CH:10]([CH2:13][NH:14][C:25]([NH:24][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N+:15]([O-:17])=[O:16])=[O:26])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 768342-Nitrophenyl isocyanateHCID 10607746[1-(Pyridin-4-yl)piperidin-4-yl]methanamine

Product 1

HCID 181744692-[1-(4-Pyridyl)piperidin-4-ylmethylaminocarbonyl]amino-nitrobenzeneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-(4-pyridyl)piperidine-4-methylamine (1.34 g, 7.01 mmol) and 2-nitrophenyl isocyanate (1.21 g, 7.40 mmol) in methylene chloride was stirred at room temperature. Concentration in vacuo and purification by flash chromatography (silica gel, 5% methanol/1% triethylamine/94% chloroform) yielded 1.59 g (64%) of the title compound.

Workup

  1. concentrationConcentration
  2. customin vacuo and purification by flash chromatography (silica gel, 5% methanol/1% triethylamine/94% chloroform)

Sources & evidence

ORD record
ord-d06460e574b847c8a97afe35270ddb3b
Source dataset
uspto-grants-2002_12
Patent number
US06500851B2

Reaction notes

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