Oxygen → 4-Piperidinodibenzofuran-1,2-dione

HRID 355602

Reaction equation

HRID 355602 reaction equation
[O:1]=O.[OH:3][C:4]1[CH:16]=[CH:15][C:7]2[O:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[C:6]=2[CH:5]=1.[NH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CO.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[N:17]1([C:15]2[C:7]3[O:8][C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:6]=3[C:5](=[O:1])[C:4](=[O:3])[CH:16]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 3

HCID 977OxygenHCID 8082PiperidineHCID 665872-Dibenzofuranol

Product 1

HCID 189401534-Piperidinodibenzofuran-1,2-dione

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 887MethanolSolvent

Procedure

Oxygen was bubbled, at a fast rate, for 3 hours, through a vigourously stirred solution of 2-hydroxydibenzofuran (73.8 g; 0.40 mol), copper (II) acetate (4.60 g; 0.025 mol) and piperidine (79.9 g; 0.94 mol) in methanol (600 ml) at room temperature. The resulting dark reaction mixture was filtered and the collected solid dried in air to give 4-piperidinodibenzofuran-1,2-dione as a very dark blue solid (66.3 g; 59%), m.pt. 151°-6° C. ##STR11##

Workup

  1. customThe resulting dark reaction mixture
  2. filtrationwas filtered
  3. customthe collected solid dried in air

Sources & evidence

ORD record
ord-4ff42388a65a429e9e97cc6099991680
Source dataset
uspto-grants-1998_11
Patent number
US05833885

Linked notes

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