Morpholine → HCID 85873132, compound

Reaction equation

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

Participants

Procedure

A mixture of 2-chloro-5-(chloromethyl)pyridine 1-oxide (1.16 g, 6.52 mmol; described in: Tilley, J. W. et al, J. Heterocyclic Chem. 1979, 16, 333), morpholine (1.14 g, 13.0 mmol), and potassium carbonate (0.90 g, 6.52 mmol) in acetonitrile (30 mL) was stirred at room temperature for 72 h. The solvent was removed in vacuo and the residue was purified on a silica gel column using chloroform/ethanol, (9:1), as the eluent affording 1.21 g (81% yield) of the title compound as a colorless solid: mp 72-74° C.; 1H NMR (CDCl3, 400 MHz) δ 8.34 (s, 1 H), 7.39 (d, J=8 Hz, 1 H), 7.16 (dd, J=8, 2 Hz, 1 H), 3.65 (t, J=5 Hz, 4 H), 3.40 (s, 2 H), 2.40 (t, J=4 Hz, 4 H); 13C NMR (CDCl3, 100 MHz) δ 140.4 (br), 135.9, 126.6, 126.6, 66.8, 59.2, 53.4; MS (ESP) m/z 229 (M++1).