Isopropanol → HCID 19012931, compound

HRID 2253696Notes

Reaction equation

HRID 2253696 reaction equation
[O:1]=[C:2]1[CH2:7][CH2:6][CH:5]([OH:8])[CH:4]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:3]1.CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O.CC(O)C>CC(C)=O>[O:1]=[C:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH:4]([CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[NH:3]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 19012860HCID 19012860, compoundHCID 131709961Jones' reagent

Product 1

HCID 19012931HCID 19012931, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a stirred solution of 2-oxo-5-hydroxy-6-benzhydryl piperidine (18.15 gm, 64.5 mmole) in acetone (150 ml) at -5° C. was added Jones reagent (2.67M, 94 mmole), and the reaction mixture was further stirred for 4 hrs. At the end of this period, the excess reactant was decomposed with 2-propanol and the solution concentrated under vacuum to half of its volume. The contents of the flask were then diluted with water (1000 ml) and extracted with methylene chloride (3×1000 ml). The combined organic phases were dried (anhyd. magnesium sulfate) and the methylene chloride was removed under vacuum to afford 2,5-dioxo-6-benzhydrylpiperidine (15.35 gm, 85%).

Workup

  1. concentrationthe solution concentrated under vacuum to half of its volume
  2. additionThe contents of the flask were then diluted with water (1000 ml)
  3. extractionextracted with methylene chloride (3×1000 ml)
  4. dry with materialThe combined organic phases were dried (anhyd. magnesium sulfate)
  5. customthe methylene chloride was removed under vacuum

Sources & evidence

ORD record
ord-0c3f2bb137544badb3813019e8bd25fa
Source dataset
uspto-grants-1993_08
Patent number
US05232929

Reaction notes

Loading…