1-(4-hydroxyiminopiperidin-1-yl)ethanone

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 23.5 g (167 mmol) of 1-acetyl-4-piperidone (Aldrich Chemical Co., Milwaukee, Wis.) and 12.5 g (179 mol) of hydroxylamine hydrochloride were placed in a 250 mL flask with 200 mL of methanol. To the resulting mixture was added 19.0 g (180 mmol) of sodium carbonate, and the resulting mixture was allowed to stir at room temperature for 12-14 h. The reaction mixture was concentrated in vacuo to afford 23.5 g of 1-acetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.72 (dd, 2H, J=11.0, 6.0 Hz), 3.59 (ddd, 2H, J=13.8, 6.2, 6.2 Hz), 2.68 (ddd, 2H, J=10.6, 6.2, 6.2 Hz), 2.42 (ddd. 2H, J=12.2, 6.1, 6.1 Hz), 2.17 (d, 3H, J=3.9 Hz); 13C NMR (75 MHz, CDCl3) δ169.39, 169.29, 156.07, 155.78, 45.95, 44.31, 41.68, 39.65, 31.27, 30.46, 25.04, 24.42, 21.47, 21.44. The reaction mixture was concentrated in vacuo

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

Procedure: 23.5 g (167 mmol) of 1-acetyl-4-piperidone (Aldrich Chemical Co., Milwaukee, Wis.) and 12.5 g (179 mol) of hydroxylamine hydrochloride were placed in a 250 mL flask with 200 mL of methanol. To the resulting mixture was added 19.0 g (180 mmol) of sodium carbonate, and the resulting mixture was allowed to stir at room temperature for 12-14 h. The reaction mixture was concentrated in vacuo to afford 23.5 g of 1-acetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.72 (dd, 2H, J=11.0, 6.0 Hz), 3.59 (ddd, 2H, J=13.8, 6.2, 6.2 Hz), 2.68 (ddd, 2H, J=10.6, 6.2, 6.2 Hz), 2.42 (ddd. 2H, J=12.2, 6.1, 6.1 Hz), 2.17 (d, 3H, J=3.9 Hz); 13C NMR (75 MHz, CDCl3) δ169.39, 169.29, 156.07, 155.78, 45.95, 44.31, 41.68, 39.65, 31.27, 30.46, 25.04, 24.42, 21.47, 21.44. The reaction mixture was concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: 1-Acetyl-piperidin-4-one oxime was prepared from 1-acetyl-piperidin-4-one and hydroxylamine using conditions of General Method 1. 1H NMR (400 MHz, DMSO-d6) δ 10.48 (1H, d, 3.2 Hz), 3.43-3.56 (4H, m), 2.48-2.56 (1H, m), 2.42 (1H, t, 6.2 Hz), 2.29-2.34 (1H, m), 2.17-2.26 (1H, m), 2.03 (3H, d, 4.2 Hz).

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

Procedure: 1-Acetyl-piperidin-4-one oxime was prepared from 1-acetyl-piperidin-4-one and hydroxylamine using conditions of General Method 1. 1H NMR (400 MHz, DMSO-d6) δ 10.48 (1H, d, 3.2 Hz), 3.43-3.56 (4H, m), 2.48-2.56 (1H, m), 2.42 (1H, t, 6.2 Hz), 2.29-2.34 (1H, m), 2.17-2.26 (1H, m), 2.03 (3H, d, 4.2 Hz).

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

Procedure: 23.5 g (167 mmol) of 1-acetyl-4-piperidone (Aldrich Chemical Co., Milwaukee, Wis.) and 12.5 g (179 mol) of hydroxylamine hydrochloride were placed in a 250 mL flask with 200 mL of methanol. To the resulting mixture was added 19.0 g (180 mmol) of sodium carbonate, and the resulting mixture was allowed to stir at room temperature for 12-14 h. The reaction mixture was concentrated in vacuo to afford 23.5 g of 1-acetyl-4-hydroxyiminopiperidine as a white solid: 1H NMR (300 MHz, CDCl3) δ3.72 (dd, 2H, J=11.0, 6.0 Hz), 3.59 (ddd, 2H, J=13.8, 6.2, 6.2 Hz), 2.68 (ddd, 2H, J=10.6, 6.2, 6.2 Hz), 2.42 (ddd. 2H, J=12.2, 6.1, 6.1 Hz), 2.17 (d, 3H, J=3.9 Hz); 13C NMR (75 MHz, CDCl3) δ169.39, 169.29, 156.07, 155.78, 45.95, 44.31, 41.68, 39.65, 31.27, 30.46, 25.04, 24.42, 21.47, 21.44. The reaction mixture was concentrated in vacuo

Conditions: temp:0.00; pressure:0.00; stir: