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

HRID 647286노트

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HRID 647286 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4e5c4b4295e74e6ab19fa2e16fce3545
출처 데이터셋
uspto-grants-1983_10
특허 번호
US04408053

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