Sodium Carbonate → 1-(4-(Hydroxyimino)piperidin-1-yl)ethanone

HRID 399194Notes

Reaction equation

HRID 399194 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.[NH2:12][OH:13].C(=O)([O-])[O-].[Na+].[Na+]>CO>[C:1]([N:4]1[CH2:9][CH2:8][C:7](=[N:12][OH:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 122563N-Acetyl-4-piperidoneHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 157079881-(4-(Hydroxyimino)piperidin-1-yl)ethanoneYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-6ca432a46b5f4b61b8a7d298cc6ed6c9
Source dataset
uspto-grants-1998_10
Patent number
US05817823

Reaction notes

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