Morpholine → HCID 85873132, compound

HRID 748505Notes

Reaction equation

HRID 748505 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

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 124874662-Chloro-5-chloromethylpyridine 1-oxide

Product 1

HCID 85873132HCID 85873132, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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).

Workup

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

Sources & evidence

ORD record
ord-4496d3a00d0c4c209153b5c859da5fea
Source dataset
uspto-grants-2008_07
Patent number
US07399780B2

Reaction notes

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