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

HRID 395706Notes

Reaction equation

HRID 395706 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-87b76a25e1584d29a9324ac07147dc37
Source dataset
uspto-grants-2003_08
Patent number
US06605626B2

Reaction notes

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