Potassium Cyanide → 1-Dimethylamino-4-hydroxyamino-piperidine-4-carbonitrile

HRID 2367890Notes

Reaction equation

[CH3:1][N:2]([CH3:11])[N:3]1[CH2:8][CH2:7][C:6](=[N:9][OH:10])[CH2:5][CH2:4]1.P([O-])(O)(O)=O.[K+].[C-:18]#[N:19].[K+]>O>[CH3:1][N:2]([CH3:11])[N:3]1[CH2:8][CH2:7][C:6]([NH:9][OH:10])([C:18]#[N:19])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: 5 °C

Procedure

12.4 g 1-Dimethylamino-piperidin-4-one oxime (from Step 1) is dissolved in 160 ml water. 49.3 g potassium dihydrogenphosphate is added. The resulting yellow suspension is cooled to 5° C., and a solution of 11.24 g potassium cyanide in 40 ml water is added. The mixture is stirred at room temperature for 2 days, then extracted with ethyl acetate, the organic layer dried over sodium sulfate, and the solvent evaporated, to give 7.8 g 1-Dimethylamino-4-hydroxyamino-piperidine-4-carbonitrile. 1H-NMR (CDCl3): 5.60 ppm (s, broad, 1H), 5.10 ppm (s, broad, 1H), 2.92 ppm (m, 2H), 2.61 ppm (m, 2H), 2.33 ppm (s, 6H), 2.10 ppm (m, 2H), 1.70 ppm (m, 2H).

Workup

extractionextracted with ethyl acetate
dry with materialthe organic layer dried over sodium sulfate
customthe solvent evaporated

Sources & evidence

ORD record: ord-16d1c233e8934ee3b70bd591f0308c4d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703165B2

Reaction notes

Loading…