Sodium Bicarbonate → 4-Piperidinone O-methyloxime hydrochloride

HRID 2221003Notes

Reaction equation

HRID 2221003 reaction equation
O=[C:2]1[CH2:7][CH2:6][N:5](C(OC(C)(C)C)=O)[CH2:4][CH2:3]1.[ClH:15].[O:16]([NH2:18])[CH3:17].C(=O)(O)[O-].[Na+]>C1COCC1.O>[ClH:15].[CH3:17][O:16][N:18]=[C:2]1[CH2:3][CH2:4][NH:5][CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 148788004-Piperidinone O-methyloxime hydrochlorideYield 128.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of tert-butyl 4-oxo-1-piperidinecarboxylate (2.0 g) and methoxylamine hydrochloride (2.93 g) in THF (66 mL) was treated with sodium bicarbonate (2.95 g) dissolved in water (20 mL). The biphasic mixture was stirred vigorously for 10 minutes, diluted with water, and extracted with ethyl acetate (×3). The combined extracts were dried over magnesium sulfate, filtered and concentrated to afford 2.12 g of the title compound, which was used without further purification. 1H NMR (CDCl3, 300 MHz) δ ppm 1.49 (s, 9H), 2.34 (t, 2H, J=6.07 Hz), 2.57 (t, 2H, J=6.07 Hz), 3.51 (t, 2H, J=6.07 Hz), 3.56 (t, 2H, J=6.07 Hz), 3.85 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-082845367b3f4034a5b1854fc705e69f
Source dataset
uspto-grants-2008_05
Patent number
US07368453B2

Reaction notes

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