Isopropanol → HCID 13076415, compound

HRID 370893Notes

Reaction equation

HRID 370893 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8](=O)[C:9]2[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=2F)[CH2:4][CH2:3]1.[OH-:18].[K+].[ClH:20].[NH2:21]O.C(O)(C)C>CCOCC.O>[ClH:20].[F:15][C:14]1[C:9]2[C:8]([CH:5]3[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]3)=[N:21][O:18][C:10]=2[CH:11]=[CH:12][CH:13]=1

Participants

7

Reactant 4

HCID 3776IsopropanolHCID 14797Potassium HydroxideHCID 443297Hydroxyamine hydrochlorideHCID 13076398HCID 13076398, compound

Product 1

HCID 13076415HCID 13076415, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

A stirred mixture of 209 g of 1-methyl-4-(2,6-difluorobenzoyl)piperidine, 400 g of potassium hydroxide, 102 g of hydroxylamine hydrochloride, 2100 ml of isopropanol and 2100 ml of water was refluxed for 10 hrs and then stirred overnight at ambient temperature. The reaction mixture was poured into water and extracted with hexane. The hexane extracts were dried over anhydrous magnesium sulfate, filtered and the solvent was removed in vacuo to yield a solid. The solid was purified by passing it through a silica gel column (15:1) using 1% methanol in dichloromethane as eluent. Evaporation of the eluent provided a solid, which was dissolved in ether. A hydrochloric acid-ether solution was added dropwise. The precipitate was collected and washed with ether to yield 24.71 g (14%) of product, mp, 221°-223°.

Workup

  1. temperaturewas refluxed for 10 hrs
  2. extractionextracted with hexane
  3. dry with materialThe hexane extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customto yield a solid
  7. customThe solid was purified
  8. customEvaporation of the eluent
  9. customprovided a solid, which
  10. customThe precipitate was collected
  11. washwashed with ether

Sources & evidence

ORD record
ord-dff706605d274b50a794463ff71b7afa
Source dataset
uspto-grants-1985_07
Patent number
US04528376

Reaction notes

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