4-Methylpiperidine → 6'-Chloro-4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinyl

HRID 646917Notes

Reaction equation

HRID 646917 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:11])[N:3]=1.[CH3:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1>C(O)C>[Cl:11][C:4]1[N:3]=[C:2]([N:16]2[CH2:17][CH2:18][CH:13]([CH3:12])[CH2:14][CH2:15]2)[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 693814-MethylpiperidineHCID 852392,6-Dichloro-3-nitropyridine

Product 1

HCID 431526786'-Chloro-4-methyl-3'-nitro-3,4,5,6-tetrahydro-2H-[1,2']bipyridinylYield 45.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A flask was charged with 2,6-dichloro-3-nitropyridine (1.00 g, 5.00 mmol), absolute ethanol (25 mL), and 4-methylpiperidine (0.65 mL, 5.5 mmol) and stirred 15 h at RT. The solvents were removed in vacuo and purification of the resulting residue by silica gel preparative TLC eluting with 10% ethyl acetate in hexane yielded 577 mg (45%) of the title compound as a yellow glass. LC-MS (ESI, m/z): Calcd. for C11H15ClN3O2, 256.1/258.1 (M+H); found: 256.1/258.1.

Workup

  1. customThe solvents were removed in vacuo and purification of the resulting residue by silica gel preparative TLC
  2. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3a74d5d793134941b092a0495f4386b8
Source dataset
uspto-grants-2010_04
Patent number
US07705042B2

Reaction notes

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