Hydroxyamine hydrochloride → 1-Acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine oxime
Reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[OH:19])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.[NH2:22][OH:23].C([O-])(=O)C.[NH4+]>O>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[N:22][OH:23])[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[CH:14]=[CH:13][C:12]=2[OH:19])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
Procedure
A solution of 15.5 g of 1-acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine, 7.0 g of hydroxylamine hydrochloride, 9.5 g of ammonium acetate and 75 ml of water was heated under reflux for 20 hrs. The solution was poured into water and extracted with dichloromethane. The dichloromethane extract was washed with water, dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give an oil. The oil was triturated with hot toluene. The toluene was decanted and the oil was triturated with ether to give a solid. The tolulene triturant, upon standing, yielded a solid. The solids were combined and recrystallized from acetonitrile to yield 2.8 g (17.4%) of product, mp, 191°-193°, as a mixture of E- and Z-isomers. The chromatogram showed 2 spots.
Workup
- temperatureunder reflux for 20 hrs
- extractionextracted with dichloromethane
- extractionThe dichloromethane extract
- washwas washed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent was removed in vacuo
- customto give an oil
- customThe oil was triturated with hot toluene
- customThe toluene was decanted
- customthe oil was triturated with ether
- customto give a solid
- customyielded a solid
- customrecrystallized from acetonitrile
Sources & evidence
- ORD record
- ord-1b85797003b1489cb3dabf1d4a71a1a3
- Source dataset
- uspto-grants-1985_07
- Patent number
- US04528376
Reaction notes
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