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

HRID 574619

Reaction equation

[NH2:1][CH2:2][C:3]1([OH:10])[CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]1.S([O-])([O-])(=O)=O.[Mg+2].[CH:17](=O)[CH3:18]>ClCCl>[CH3:17][CH:18]1[NH:1][CH2:2][C:3]2([CH2:8][CH2:7][N:6]([CH3:9])[CH2:5][CH2:4]2)[O:10]1

Participants

Conditions

Temperature: 0 °C

Procedure

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.

Workup

filtrationthe mixture was filtered
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-a667713d7ea740cc8466bb9ded0c2186
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034891B2

Linked notes

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