Hydroxyamine hydrochloride → 1-Acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine oxime

HRID 370886ノート

反応式

HRID 370886 の反応式
[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]

参加物

5

反応物 3

HCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 130763841-Acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine

生成物 1

HCID 1364088731-Acetyl-4-(2-hydroxy-5-methoxybenzoyl)piperidine oxime収率 17.4%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

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.

後処理

  1. temperatureunder reflux for 20 hrs
  2. extractionextracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. washwas washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was removed in vacuo
  7. customto give an oil
  8. customThe oil was triturated with hot toluene
  9. customThe toluene was decanted
  10. customthe oil was triturated with ether
  11. customto give a solid
  12. customyielded a solid
  13. customrecrystallized from acetonitrile

出典と根拠

ORDレコード
ord-1b85797003b1489cb3dabf1d4a71a1a3
出典データセット
uspto-grants-1985_07
特許番号
US04528376

反応ノート

読み込み中…