Methylamine → HCID 19002983, compound

Temperature

0 °C

3,6-Dihydro-4-(1-naphthalenyl)-1(2H)-pyridinepropanol (Ex. 4: 1.20 g, 4.49 mmol) was dissolved in chloroform (50 mL) followed by the addition of triethylamine (0.94 mL, 6.73 mmol) and cooled to 0° C. Methanesulfonyl chloride (0.42 mL, 5.39 mmol) was added dropwise and the reaction was allowed to stir for thirty minutes while warming to room temperature. Solvent was then removed in vacuo yielding a crude solid (IV). This material was then dissolved in a solution of acetonitrile (60 mL) containing 40 wt. % aqueous methylamine (60 mL) and heated at reflux for three hours. The reaction was cooled to room temperature and concentrated in vacuo. The crude residue was diluted with chloroform (500 mL) and washed with aqueous 10% potassium carbonate (200 mL) followed by saturated aqueous sodium chloride (200 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated yielding 1.20 g (98%) of the title compound as a viscous golden oil: 1H NMR (CDCl3): δ 1.80 (m, 2H), 2.05 (br s, 1H), 2.43 (s, 3H), 2.57 (m, 2H), 2.70 (t, J=Hz, 2H), 2.79 (t, J=Hz, 2H), 3.20 (m, 2H), 5.73 (m, 1H), 7.25 (d, J=1.58, 1H), 7.39-7.48 (m, 3H), 7.75 (d, J=8.19, 1H), 7.83 (m, 1H), 7.96 (m, 1H)

1. temperaturewhile warming to room temperature
2. customSolvent was then removed in vacuo
3. customyielding a crude solid (IV)
4. temperatureheated
5. temperatureat reflux for three hours
6. temperatureThe reaction was cooled to room temperature
7. concentrationconcentrated in vacuo
8. additionThe crude residue was diluted with chloroform (500 mL)
9. washwashed with aqueous 10% potassium carbonate (200 mL)
10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
11. filtrationfiltered
12. concentrationconcentrated

ORD record

ord-72a7b36fe33245ceb625b213c052b165

Source dataset

uspto-grants-1995_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05472966