Methanol → HCID 53732176, compound
Reaction equation
CO.[OH:3][CH:4]1[C:10]([CH3:12])([CH3:11])[CH2:9][C:8](=O)[C:7]([CH3:14])=[CH:6][CH:5]1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.Cl.[CH3:22][O:23][NH2:24].[OH-].[Na+]>O.N1C=CC=CC=1>[CH3:22][O:23][N:24]=[C:8]1[CH2:9][C:10]([CH3:12])([CH3:11])[CH:4]([OH:3])[CH:5]([N:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:6]=[C:7]1[CH3:14]Participants
Procedure
To a methanol solution (30 ml) containing the 5-hydroxy-4-piperidino-2,6,6-trimethyl-2-cyclohepten-1-one obtained in Example 16 (3 g, 12.5 millimoles) were added methoxyamine hydrochloride (1.57 g, 18.8 millimoles) and pyridine (3.0 g), and the mixture was stirred first at room temperature and then while slowly heating to 55° C., and after 5 hours of stirring at that temperature, it was allowed to stand at room temperature overnight. The reaction solution was then poured into water and alkalified with a 10% aqueous sodium hydroxide solution (20 ml). The aqueous solution was subjected to extraction with benzene and dried over anhydrous magnesium sulfate. The benzene solution was concentrated under reduced pressure, to obtain 3.49 g of 5-hydroxy-4-piperidino-2,6,6-trimethyl-2-cyclohepten-1-one methyloxime as crude crystals.
Workup
- temperaturewhile slowly heating to 55° C.
- stirringafter 5 hours of stirring at that temperature, it
- extractionThe aqueous solution was subjected to extraction with benzene
- dry with materialdried over anhydrous magnesium sulfate
- concentrationThe benzene solution was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-dd117496b1b847cb91f0d9d929c591de
- Source dataset
- uspto-grants-1998_12
- Patent number
- US05849801
Reaction notes
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