Ethanol → HCID 21699693, compound

HRID 1597277Notes

Reaction equation

HRID 1597277 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=O)[C:2]1=[O:3].[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22](=O)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C([OH:28])C>[OH-].[K+]>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][C:22]2[N:1]=[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]3=[C:4]([C:2]([OH:28])=[O:3])[C:21]=2[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 702EthanolHCID 7054IsatinHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylate

Product 1

HCID 21699693HCID 21699693, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideCatalyst

Procedure

Isatin (14.71 g, 100 mmol) and 1-t-butoxycarbonyl-4-piperidone (19.93 g, 100 mmol) were dissolved in ethanol (200 ml), followed by adding thereto an ethanolic solution (50 ml) of KOH (12.34 mg), and the resulting mixture was stirred at 70° C. for 24 hours. The solvent was removed by concentration under reduced pressure, and the residue was neutralized with acetic acid. The resulting insoluble material was purified by suspension in methanol to obtain the desired compound (9.5 g, 29%) as a light-brownish-white substance.

Workup

  1. additionby adding
  2. customThe solvent was removed by concentration under reduced pressure
  3. customThe resulting insoluble material was purified by suspension in methanol

Sources & evidence

ORD record
ord-bde2058d63c348c387ab6d15db2234b5
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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