1,2-Difluoro-3-nitrobenzene → N-Nitropiperidine

HRID 467544Notes

Reaction equation

HRID 467544 reaction equation
FC1C=CC=C([N+:8]([O-:10])=[O:9])C=1F.[NH:12]1[CH2:17][CH2:16][CH2:15][C@@H:14](NC(=O)OC(C)(C)C)[CH2:13]1>C(#N)C.C(N(CC)C(C)C)(C)C>[N+:8]([N:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([O-:10])=[O:9]

Participants

5

Reactant 2

HCID 813351,2-Difluoro-3-nitrobenzeneHCID 1514172(3R)-3-Aminopiperidine, 3-BOC protected

Product 1

HCID 23506N-NitropiperidineYield 189,532%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 1,2-difluoro-3-nitrobenzene (2.38 g, 0.015 mmol), (R)-tert-butyl piperidin-3-ylcarbamate (3.0 g, 0.015 mmol) and N,N-diisopropylethylamine (5.2 ml, 0.030 mmol) was heated in acetonitrile (20 mL) at 80° C. overnight. The solvents were removed in vacuo, and chromatographic purification (ethyl acetate-hexanes) of the residue gave a nitropiperidine as orange oil (3.7 g, 72%).

Workup

  1. customThe solvents were removed in vacuo, and chromatographic purification (ethyl acetate-hexanes) of the residue

Sources & evidence

ORD record
ord-04ddb2a1b1ad4d77940e5cb2a783b53f
Source dataset
uspto-grants-2014_01
Patent number
US08623857B2

Reaction notes

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