1-Fluoro-2-nitrobenzene → tert-Butyl (1-(2-nitrophenyl)piperidin-4-yl)carbamate

HRID 1500268Notes

Reaction equation

HRID 1500268 reaction equation
F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].C(N(CC)C(C)C)(C)C.[C:20]([O:24][C:25](=[O:33])[NH:26][CH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([CH3:23])([CH3:22])[CH3:21]>O1CCOCC1>[C:20]([O:24][C:25](=[O:33])[NH:26][CH:27]1[CH2:32][CH2:31][N:30]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:29][CH2:28]1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 738951-Fluoro-2-nitrobenzeneHCID 81531DiisopropylethylamineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 53255688tert-Butyl (1-(2-nitrophenyl)piperidin-4-yl)carbamateYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 1-fluoro-2-nitro-benzene (0.50 mmol, 53 μL), N,N-diisopropylethylamine (0.50 mmol, 87 μL) and Piperidin-4-yl-carbamic acid tert-butyl ester (0.50 mmol, 0.10 g) in 1,4-dioxane (2 mL) was irradiated using microwave for 10 minutes at a temperature of 180° C. The solution was then cooled to room temperature and concentrated in vacuo and the resulting residue was purified using column chromatography on silica gel to provide [1-(2-Nitro-phenyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.12 g, 77% yield). To the solution of this nitro compound in EtOAc (15 mL) was added Pd on carbon (5% Pd, 55 mg). The resulting reaction mixture was stirred under a hydrogen atmosphere at room temperature for about 15 hours. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated in vacuo to provide Intermediate Compound 42A (97 mg, 86% yield).

Workup

  1. customfor 10 minutes
  2. customat a temperature of 180° C
  3. concentrationconcentrated in vacuo
  4. customthe resulting residue was purified

Sources & evidence

ORD record
ord-c4eb6260bfc347049477c665b8a3432e
Source dataset
uspto-grants-2015_12
Patent number
US09206142B2

Reaction notes

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