Acetaldehyde → 2,8-Dimethyl-1-oxa-3,8-diazaspiro[4.5]decane

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-aminomethyl-1-methyl-piperidin-4-ol (2.127 g, 14.77 mmol) in dichloromethane (15 ml) was added anhydrous magnesium sulfate (2.9 g). The resulting mixture was cooled to 0° C. and freshly distilled acetaldehyde (835 μl, 14.78 mmol) was added. After 6 h of stirring at room temperature, the mixture was filtered and the solvent was evaporated under reduced pressure to give the title compound (2.16 g) as an almost colorless liquid. 1H NMR (CDCl3, 500 MHz) δ 4.60 (q, J=5.40 Hz, 1H, CHCH3), 3.01 (d, J=12 Hz, 1H, CHHNH), 2.76 (d, J=12 Hz, 1H, CHHNH), 2.55-2.31 (m, 4H, CH2N), 2.28 (s, 3H, NCH3), 1.77-1.58 (m, 4H, CH2CO), 1.36 (d, J=5.40 Hz, 3H, CH3CH) ppm; 13C NMR (CDCl3, 300 MHz) δ 87.57 (CH), 57.19 (CH2), 53.14 (C), 52.96 (CH2), 46.15 (CH3), 37.28 (CH2), 35.73 (CH2), 20.32 (CH3) ppm.

Provenance & Evidence