Isopropanol → HCID 19012931, compound

HRID 1729476Notes

Reaction equation

HRID 1729476 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 (2.67 M, 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 dilutes 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. extractionextracted with methylene chloride (3×1000 ml)
  3. dry with materialthe combined organic phases were dried (anhyd. magnesium sulfate)
  4. customthe methylene chloride was removed under vacuum

Sources & evidence

ORD record
ord-387843334e13488daa217ae16ca7bc64
Source dataset
uspto-grants-1994_07
Patent number
US05332817

Reaction notes

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