Methylamine → 1-Dimethylamino-4-methylamino-piperidine-4-carbonitrile

HRID 2367884Notes

Reaction equation

HRID 2367884 reaction equation
[CH3:1][N:2]([CH3:10])[N:3]1[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.Cl.[CH3:12][NH2:13].[CH3:14][NH2:15].[C-]#N.[K+]>O>[CH3:1][N:2]([CH3:10])[N:3]1[CH2:8][CH2:7][C:6]([NH:15][CH3:14])([C:12]#[N:13])[CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 9032Potassium CyanideHCID 6364545Methylamine hydrochlorideHCID 567377821-(Dimethylamino)-4-piperidinone

Product 1

HCID 672253971-Dimethylamino-4-methylamino-piperidine-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

5.5 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961), 4.2 g methylamine hydrochloride and 4.9 ml methylamine solution (40% in water) are mixed in 35 ml water, then to this mixture a solution of 4 g potassium cyanide in 10 ml water is added. The resulting mixture is stirred at room temperature for 3 days, then extracted with ethyl acetate, the organic layer dried over sodium sulfate, and the solvent evaporated. 5.3 g 1-Dimethylamino-4-methylamino-piperidine-4-carbonitrile is obtained. 1H-NMR (CDCl3): 2.86 ppm (m, 2H), 2.57 ppm (m, 2H), 2.44 ppm (s, 3H), 2.32 ppm (s, 6H), 2.00 ppm (m, 2H), 1.69 ppm (m, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialthe organic layer dried over sodium sulfate
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-9cdbaf4bb1e74539b2d084de1c4c3ae6
Source dataset
uspto-grants-2014_04
Patent number
US08703165B2

Reaction notes

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