Piperidine → HCID 53884104, compound

HRID 1940683Notes

Reaction equation

HRID 1940683 reaction equation
[Br:1][C:2]1[C:3]([OH:11])=[C:4]([OH:10])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[S:12]([CH2:18][C:19]#[N:20])([CH2:15][C:16]#[N:17])(=[O:14])=[O:13].N1CCCCC1>C(O)C>[Br:1][C:2]1[CH:9]=[C:6]([CH:7]=[C:15]([C:16]#[N:17])[S:12]([CH2:18][C:19]#[N:20])(=[O:14])=[O:13])[CH:5]=[C:4]([OH:10])[C:3]=1[OH:11]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 854055-Bromo-3,4-dihydroxybenzaldehydeHCID 142163Sulphonyl diacetonitrile

Product 1

HCID 53884104HCID 53884104, compoundYield 6.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 500 mg of 5-bromo-3,4-dihydroxybenzaldehyde and 700 mg of sulfonyl diacetonitrile in 6 ml of ethanol was refluxed with few drops of piperidine for 4 hours. Ethanol was removed in rotavap and the mixture worked up with ethyl acetate, diluted acid and brine. A portion of the crude was then purified by HPLC on a C-18 column to provide about 50 mg of 2-(3-bromo-4,5-dihydroxyphenyl)-1-cyano-1-cyanomethylsulfonyl ethene.

Workup

  1. customEthanol was removed in rotavap
  2. additiondiluted acid and brine
  3. customA portion of the crude was then purified by HPLC on a C-18 column

Sources & evidence

ORD record
ord-536a5d093d1b4875a2d35c81bf12ac24
Source dataset
uspto-grants-1997_12
Patent number
US05700822

Reaction notes

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