1-(dimethylamino)piperidin-4-one

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) is cooled to 0° C., and 3.8 g N,N-dimethylhydrazine is added at such a rate, that the internal temperature does not exceed 15° C. The mixture is stirred at ambient temperature for 3 hours. Then the excess of N,N-dimethylhydrazine is evaporated. Thus, 3.65 g [4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine is obtained. 1H-NMR (CDCl3): 2.80 ppm (m, 2H), 2.70 ppm (m, 4H), 2.45 ppm (s, 6H), 2.42 ppm (m, 2H), 2.40 ppm (s, 6H). does not exceed 15° C Then the excess of N,N-dimethylhydrazine is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) is cooled to 0° C., and 3.8 g N,N-dimethylhydrazine is added at such a rate, that the internal temperature does not exceed 15° C. The mixture is stirred at ambient temperature for 3 hours. Then the excess of N,N-dimethylhydrazine is evaporated. Thus, 3.65 g [4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine is obtained. 1H-NMR (CDCl3): 2.80 ppm (m, 2H), 2.70 ppm (m, 4H), 2.45 ppm (s, 6H), 2.42 ppm (m, 2H), 2.40 ppm (s, 6H). does not exceed 15° C Then the excess of N,N-dimethylhydrazine is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 3.0 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) is cooled to 0° C., and 3.8 g N,N-dimethylhydrazine is added at such a rate, that the internal temperature does not exceed 15° C. The mixture is stirred at ambient temperature for 3 hours. Then the excess of N,N-dimethylhydrazine is evaporated. Thus, 3.65 g [4-(Dimethyl-hydrazono)-piperidin-1-yl]-dimethyl-amine is obtained. 1H-NMR (CDCl3): 2.80 ppm (m, 2H), 2.70 ppm (m, 4H), 2.45 ppm (s, 6H), 2.42 ppm (m, 2H), 2.40 ppm (s, 6H). does not exceed 15° C Then the excess of N,N-dimethylhydrazine is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6.0 g 1-dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) in 30 ml of dichloromethane is added to a mixture of 4.1 g potassium cyanide and 10.6 g sodium hydrogencarbonate in 30 ml of water. The resulting mixture is stirred at room temperature for 3 hours, then extracted with ethyl acetate, the organic layer dried over sodium sulfate, and the solvent evaporated. 4.8 g 1-Dimethylamino-4-hydroxy-piperidine-4-carbonitrile is obtained. 1H-NMR (CDCl3): 3.95 ppm (s, broad, 1H), 2.90 ppm (m, 2H), 2.68 ppm (m, 2H), 2.40 ppm (s, 6H), 2.15 ppm (m, 2H), 1.95 ppm (m, 2H). extracted with ethyl acetate the organic layer dried over sodium sulfate the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 6.0 g 1-dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) in 30 ml of dichloromethane is added to a mixture of 4.1 g potassium cyanide and 10.6 g sodium hydrogencarbonate in 30 ml of water. The resulting mixture is stirred at room temperature for 3 hours, then extracted with ethyl acetate, the organic layer dried over sodium sulfate, and the solvent evaporated. 4.8 g 1-Dimethylamino-4-hydroxy-piperidine-4-carbonitrile is obtained. 1H-NMR (CDCl3): 3.95 ppm (s, broad, 1H), 2.90 ppm (m, 2H), 2.68 ppm (m, 2H), 2.40 ppm (s, 6H), 2.15 ppm (m, 2H), 1.95 ppm (m, 2H). extracted with ethyl acetate the organic layer dried over sodium sulfate the solvent evaporated

Conditions: temp:37.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 19.2 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) and 30 g triethylamine are dissolved in 80 ml methanol. 18.8 g hydroxylamin hydrochloride is added in portions at ambient temperature. The internal temperature raises during the addition to 37° C. Then the mixture is heated to reflux for 3 hours, allowed to cool to room temperature, and then the solvent evaporated. The residue is partitioned between ethyl acetate and aqueous sodium bicarbonate. The organic layer is dried over sodium sulfate, and the solvent evaporated. Thus, 14.5 g 1-Dimethylamino-piperidin-4-one oxime is obtained. 1H-NMR (CDCl3): 8.10 ppm (s, broad, 1H), 2.75 ppm (m, 6H), 2.40 ppm (m, 2H), 2.40 ppm (s, 6H). Then the mixture is heated to reflux for 3 hours to cool to room temperature the solvent evaporated The residue is partitioned between ethyl acetate and aqueous sodium bicarbonate The organic layer is dried over sodium sulfate the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). extracted with ethyl acetate the organic layer dried over sodium sulfate the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

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). extracted with ethyl acetate the organic layer dried over sodium sulfate the solvent evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.3 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) is dissolved in 135 ml aqueous ammonia (25%). To this solution 3.55 g ammonium chloride is added, then 4.34 g sodium cyanide. The reaction mixture is stirred at room temperature for 18 hours. Then the mixture is saturated with sodium chloride, and four times extracted with ethyl acetate. The organic layer is dried over sodium sulfate, and the solvent is evaporated, to yield 5.6 g 4-Amino-1-dimethylamino-piperidine-4-carbonitrile as a yellow oil. 1H-NMR (CDCl3): 2.95 ppm (m, 2H), 2.65 ppm (m, 2H), 2.40 ppm (s, 6H), 2.05 ppm (m, 2H), 1.80 ppm (m, 2H), 1.75 ppm (s, broad, 2H). extracted with ethyl acetate The organic layer is dried over sodium sulfate the solvent is evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 6.3 g 1-Dimethylamino-piperidin-4-one (prepared as described in Journal of Medicinal & Pharmaceutical Chemistry, 4, 423-36; 1961) is dissolved in 135 ml aqueous ammonia (25%). To this solution 3.55 g ammonium chloride is added, then 4.34 g sodium cyanide. The reaction mixture is stirred at room temperature for 18 hours. Then the mixture is saturated with sodium chloride, and four times extracted with ethyl acetate. The organic layer is dried over sodium sulfate, and the solvent is evaporated, to yield 5.6 g 4-Amino-1-dimethylamino-piperidine-4-carbonitrile as a yellow oil. 1H-NMR (CDCl3): 2.95 ppm (m, 2H), 2.65 ppm (m, 2H), 2.40 ppm (s, 6H), 2.05 ppm (m, 2H), 1.80 ppm (m, 2H), 1.75 ppm (s, broad, 2H). extracted with ethyl acetate The organic layer is dried over sodium sulfate the solvent is evaporated