4-Chloro-3-nitropyridine → HCID 58386784, compound

HRID 924448Notes

Reaction equation

HRID 924448 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].[CH3:11][C@H:12]1[CH2:17][NH:16][CH2:15][C@@H:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13]1>C(O)(C)C>[CH3:11][C@H:12]1[CH2:17][N:16]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N+:8]([O-:10])=[O:9])[CH2:15][C@@H:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:13]1

Participants

4

Reactant 2

HCID 27357814-Chloro-3-nitropyridineHCID 57433105tert-Butyl ((3S,5R)-5-methylpiperidin-3-yl)carbamate

Product 1

HCID 58386784HCID 58386784, compoundYield 76.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 4-chloro-3-nitropyridine (0.704 g, 4.44 mmol) and tert-butyl [(3S,5R)-5-methylpiperidin-3-yl]carbamate (1.0 g, 4.7 mmol) in isopropyl alcohol (8.7 mL) was stirred at 75° C. overnight. The mixture was concentrated under reduced pressure, and the resulting residue was diluted with water and extracted with EtOAc. The organic extracts were combined and evaporated under reduced pressure. The residue was purified by flash chromatography on 40 g silica gel, eluting with 0-90% EtOAc in hexanes, to give the sub-title compound as a yellow solid (1.14 g, 76.2%). LCMS calc. for C16H25N4O4 (M+H)+: m/z=337.2. found: 337.3.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with water
  3. extractionextracted with EtOAc
  4. customevaporated under reduced pressure
  5. customThe residue was purified by flash chromatography on 40 g silica gel
  6. washeluting with 0-90% EtOAc in hexanes

Sources & evidence

ORD record
ord-6ce2661aee084cf69b978e6ed7d5ed46
Source dataset
uspto-grants-2016_03
Patent number
US09278950B2

Reaction notes

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