Potassium Carbonate → HCID 86038278, compound

HRID 2245550Notes

Reaction equation

HRID 2245550 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]Cl)=[CH:4][N+:3]=1[O-:10].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[Cl:1][C:2]1[N+:3]([O-:10])=[CH:4][C:5]([CH2:8][N:15]2[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 531671-MethylpiperazineHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 86038278HCID 86038278, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-chloro-5-(chloromethyl)pyridine 1-oxide (0.5 g, 2.8 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333), 1-methylpiperazine (0.34 g, 3.37 mmol), and potassium carbonate (0.78 g, 5.62 mmol) in acetonitrile (5 mL) was stirred at room temperature for 13 h. The solvent was removed in vacuo and the residue was purified on a silica gel column using a gradient dichloromethane/methanol, (100:1 to 2:1), as the eluent affording 0.57 g (84% yield) of the title compound as a colorless solid: 1H NMR (CDCl3, 400 MHz) δ 8.34 (s, 1H), 7.38 (d, J=8 Hz, 1H), 7.12 (d, J=8 Hz, 1H), 3.42 (s, 2H), 2.52 (s, 8H), 2.34 (m, 3H); 13C NMR (CDCl3, 100 MHz) δ 140.6, 140.6, 136.3, 126.7, 58.9, 55.0, 52.6, 45.8; MS (ESP) m/z 242 (M++1).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-fd6142df3d2c4ede8ea7a37253208300
Source dataset
uspto-grants-2010_03
Patent number
US07683067B2

Reaction notes

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