Sodium Nitrite → HCID 66862724, compound

Participants

Reaction Conditions

Reaction Steps

To 4-(4,6-dimethyl-pyridin-2-yl)-morpholine (9.4 g) dissolved in trifluoroacetic acid (250 mL) cooled to 0° C. was added sodium nitrite (3.54 g) over 15 minutes and the reaction mixture was then stirred 15 minutes at 0° C. The reaction mixture was concentrated in vacuo to app. 100 mL and the pH adjusted to 11 with concentrated aqueous sodium hydroxide (150 mL). Brine (200 mL) was added and the mixture was extracted with diethyl ether (4×150 mL), the organic phase was dried over magnesium sulfate and concentrated in vacuo. The crude product was subjected to flash chromatography (SiO2, heptane/ethylacetate 4:1) to furnish 2.01 g (17% yield) of the title compound as a yellow solid. GC-MS (m/z) 237 (M+); tR=7.69. 1H NMR (500 MHz, DMSO-d6): 2.28 (s, 3H), 2.39 (s, 3H), 3.60 (m, 4H), 3.67 (m, 4H), 6.72 (s, 1H).

Provenance & Evidence