2-Nitrophenyl isocyanate → 2-Nitro-N-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)benzeneamine

HRID 427556Notes

Reaction equation

HRID 427556 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]=[C:11]=[O:12])([O-:3])=[O:2].N1C=CC([N:19]2[CH2:24][CH2:23][CH:22]([CH2:25][OH:26])[CH2:21][CH2:20]2)=CC=1>C(Cl)Cl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([O:26][CH:25]([CH:22]1[CH2:21][CH2:20][NH:19][CH2:24][CH2:23]1)[C:22]1[CH:23]=[CH:24][N:19]=[CH:20][CH:21]=1)=[O:12])([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 768342-Nitrophenyl isocyanateHCID 11310048(1-(Pyridin-4-YL)piperidin-4-YL)methanol

Product 1

HCID 700319012-Nitro-N-[1-(4-pyridyl)piperidin-4-ylmethoxycarbonyl)benzeneamineYield 197.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-nitrophenyl isocyanate (4.25 g, 25.9 mmol) and 1-(4-pyridyl)piperidine-4-methanol (4.13 g, 21.5 mmol) in methylene chloride (100 mL) was stirred at room temperature for 18 h. The mixture was concentrated in vacuo and the residue purified by flash chromatography (silica gel, 5% methanol/1% triethylamine/94% chloroform) to yield 7.55 g (96%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue purified by flash chromatography (silica gel, 5% methanol/1% triethylamine/94% chloroform)

Sources & evidence

ORD record
ord-c0f477298cfa418d934190082207b424
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Reaction notes

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