2-Nitrophenyl isocyanate → 2-Nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]aniline

HRID 842380Notes

Reaction equation

HRID 842380 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].[N:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([CH2:25][OH:26])[CH2:21][CH2:20]2)=[CH:15][CH:14]=1>ClCCl>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]([O:26][CH2:25][CH:22]1[CH2:21][CH2:20][N:19]([C:16]2[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=2)[CH2:24][CH2:23]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 181746182-Nitro-N-[[1-(4-pyridyl)piperidin-4-yl]methoxycarbonyl]anilineYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-nitrophenyl isocyanate (4.25 g, 25.9 mmol) and 1-(4-pyridyl)-4-piperidinemethanol (4.13 g, 21.5 mmol) in dichloromethane (100 mL) was stirred at room temperature overnight (about 18 h). The mixture was concentrated and the residue purified by flash chromatography (SiO2; CHCl3 to 5% MeOH/1% Et3N in CHCl3) to yield 7.55 g (96%) of the title compound.

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue purified by flash chromatography (SiO2; CHCl3 to 5% MeOH/1% Et3N in CHCl3)

Sources & evidence

ORD record
ord-5ed6107ff9c84691bec4a3b97ff7cdac
Source dataset
uspto-grants-2002_04
Patent number
US06372759B1

Reaction notes

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