Hydroxylamine → N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-ylidene]hydroxylamine

HRID 131775Notes

Reaction equation

HRID 131775 reaction equation
[CH2:1]([C:3]1([CH3:23])[CH:8]([CH3:9])[C:7](=O)[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[N:4]1[O:14][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[CH3:2].[NH2:24][OH:25]>CO.[OH-].[K+]>[CH2:1]([C:3]1([CH3:23])[CH:8]([CH3:9])[C:7](=[N:24][OH:25])[CH2:6][C:5]([CH2:12][CH3:13])([CH3:11])[N:4]1[O:14][CH:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])[CH3:2]

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 223418482,6-Diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-one2×

Product 1

HCID 71362831N-[2,6-Diethyl-2,3,6-trimethyl-1-(1-phenylethoxy)piperidin-4-ylidene]hydroxylamineYield 64.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14797Potassium HydroxideSolvent

Procedure

2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-4-oxopiperidine prepared according to DE 199 09 767 A1 is dissolved in methanol containing 10% by weight of KOH and stirred for 5 hours at room temperature. Methanol is evaporated, the residue is washed with water and dried in vacuo. A solution of 95.24 g (0.3 mol) of 2,6-diethyl-2,3,6-trimethyl-1-(1-phenyl-ethoxy)-4-oxopiperidine and 29.7 g (0.45 mol) 50% aqueous hydroxylamine solution in 150 ml of methanol is stirred under reflux during 5 h. The suspension is then cooled to −8° C. and filtered. The solid is washed with 100 ml of a cold (−20° C.) methanol and dried to afford 64 g (64.1%) of the title compound as a white, microcrystalline powder, mp 130-145 oC. C20H32N2O2 (332.49) calculated C 72.25%, H 9.70%, N 8.43%; found 72.19% C, 9.54% H, 8.43% N.

Workup

  1. customMethanol is evaporated
  2. washthe residue is washed with water
  3. customdried in vacuo
  4. temperatureunder reflux during 5 h
  5. temperatureThe suspension is then cooled to −8° C.
  6. filtrationfiltered
  7. washThe solid is washed with 100 ml of a cold (−20° C.) methanol
  8. customdried

Sources & evidence

ORD record
ord-b24b0c0dbd634323ad19a5fed48e831c
Source dataset
uspto-grants-2008_06
Patent number
US07385009B2

Reaction notes

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