2-Chloro-3-nitropyridine → HCID 44120582, compound

HRID 2233835Notes

Reaction equation

HRID 2233835 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Cl[C:16]1[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1>CN1C(=O)CCC1>[N+:22]([C:21]1[C:16]([N:11]2[CH2:12][CH2:13][CH:8]([NH:7][C:6](=[O:14])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:9][CH2:10]2)=[N:17][CH:18]=[CH:19][CH:20]=1)([O-:24])=[O:23]

Participants

4

Reactant 2

HCID 796132-Chloro-3-nitropyridineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 44120582HCID 44120582, compoundYield 83.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Anhydrous TEA (0.76 ml, 5.49 mmol) was added to piperidin-4-yl-carbamic acid tert-butyl ester (1 g, 5 mmol) and 2-chloro-3-nitro-pyridine (0.791 g, 5 mmol) in anhydrous NMP (3 ml). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 10 minutes. The brown solution was partitioned between EtOAc and water and the organic phase was washed several times with water, dried over sodium sulphate and concentrated in vacuo to give the title compound as a yellow solid (1.35 g).

Workup

  1. customat 150° C.
  2. customfor 10 minutes
  3. customThe brown solution was partitioned between EtOAc and water
  4. washthe organic phase was washed several times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fa3454866764ee1a3b191f0da1e0b2e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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