(3,4-Dihydro-2H-pyrano[2,3-b]pyridin-2-yl)MethanaMine synthesis

Yield:146949-50-0 94%

Reaction Conditions:

in toluene;

Steps:

VIII 2-Aminomethyl-2,3-dihydropyrano(2,3-b)-pyridine STR18

EXAMPLE VIII 2-Aminomethyl-2,3-dihydropyrano(2,3-b)-pyridine STR18 3.2 g (11 mmol) of the compound from Example VII and 9.2 g (150 mmol) of 2-aminoethanol are heated under nitrogen to 80° C. After 5 minutes the mixture is cooled, and the reaction mixture is partitioned between 70 ml of toluene and 92 ml of 5% strength NaCl solution. The phases are separated, and the aqueous phase is extracted with dichloromethane. The combined organic phases are dried and evaporated in vacuo. 1.7 g of the title compound are obtained as a light yellow oil. Yield: 94% of theory. NMR (CDCl₃): 1.73-1.85 (m, 1H); 1.93-2.00 (m, 3H, 2H exchange on addition of D₂ O); 2.74-2.95 (m) and 2.96 (quasi d, 4H); 4.09-4.18 (m, 1H); 6.81-6.86 (m, 1H); 7.35-7.37 (m, 1H) and 8.04-8.05 (m, 1H) ppm.

References:

US5250540,1993,A