Ethanol → HCID 136265272, compound

HRID 647287Notes

Reaction equation

HRID 647287 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=O)[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[OH:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].Cl.[NH2:21][OH:22].C([O-])(=O)C.[NH4+].C(O)C>C(OCC)(=O)C.C1CCCCC1>[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10](=[N:21][OH:22])[C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[OH:18])[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 702EthanolHCID 443297Hydroxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 130763861-[4-(5-Fluoro-2-hydroxybenzoyl)piperidin-1-yl]ethan-1-one

Product 1

HCID 136265272HCID 136265272, compoundYield 65.6%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 12.7 g of 1-acetyl-4-(5-fluoro-2-hydroxybenzoyl)piperidine, 6.6 g of hydroxylamine hydrochloride, 11.0 g of ammonium acetate and 200 ml of ethanol-ether was heated under reflux for 10 hrs. After cooling, most of the ethanol was removed under reduced pressure. The resultant suspension was diluted with water and extracted with dichloromethane. The dichloromethane was evaporated in vacuo to give an oil. The oil was dissolved in ethyl acetate and cyclohexane was added to precipitate a solid. The solid was recrystallized from ethyl acetate to give 8.8 g (65.4%) of product, mp, 181°-183°. The chromatogram showed 2 spots.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 10 hrs
  3. customwas removed under reduced pressure
  4. additionThe resultant suspension was diluted with water
  5. extractionextracted with dichloromethane
  6. customThe dichloromethane was evaporated in vacuo
  7. customto give an oil
  8. customto precipitate a solid
  9. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b36af5018e7948d395575f0be9f38720
Source dataset
uspto-grants-1983_10
Patent number
US04408053

Reaction notes

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