Pyridine → HCID 21478738, compound

HRID 2292488Notes

Reaction equation

HRID 2292488 reaction equation
[CH2:1]([N:5]1[CH:10]2[CH2:11][C:12](=O)[CH2:13][CH:6]1[CH2:7][O:8][CH2:9]2)[CH2:2][CH2:3][CH3:4].N1C=CC=CC=1.Cl.[NH2:22][OH:23].C(=O)([O-])[O-].[K+].[K+]>C(O)C.O>[CH2:1]([N:5]1[CH:10]2[CH2:11][C:12](=[N:22][OH:23])[CH2:13][CH:6]1[CH2:7][O:8][CH2:9]2)[CH2:2][CH2:3][CH3:4]

Participants

7

Reactant 4

HCID 1049PyridineHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 21478765HCID 21478765, compound

Product 1

HCID 21478738HCID 21478738, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 9-(n-butyl)-3-oxa-9-azabicyclo-[3.3.1]-nonan-7-one (28 g) in ethanol (150 ml) were added in turn pyridine (18.0 ml) and hydroxylamine hydrochloride (11.9 g) and the mixture was heated under reflux for 40 minutes. To the reaction solution were added water (29 ml) and potassium carbonate (57.9 g), the mixture was stirred for 30 minutes and dried over potassium carbonate. The solvent was distilled off under reduced pressure to give the crude 9-(n-butyl)-3-oxa-9-azabicyclo[3.3.1]nonan-7-one oxime. This product was employed for the sebsequent reaction without any purification.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 40 minutes
  3. dry with materialdried over potassium carbonate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dd02c8203115411b8acb92f751ce16cf
Source dataset
uspto-grants-1997_11
Patent number
US05684003

Reaction notes

Loading…