Piperidine → 4',5,7-Trihydroxy-2-piperidinomethylisoflavone

HRID 1905055Notes

Reaction equation

HRID 1905055 reaction equation
[OH:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][C:11]([OH:18])=[CH:12][C:13]=3[OH:17])[O:8][C:7]=2[CH2:19]Br)=[CH:4][CH:3]=1.[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>CN(C)C=O>[OH:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]2[C:15](=[O:16])[C:14]3[C:9](=[CH:10][C:11]([OH:18])=[CH:12][C:13]=3[OH:17])[O:8][C:7]=2[CH2:19][N:23]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 155987314',5,7-Trihydroxy-2-bromomethylisoflavone

Product 1

HCID 155987354',5,7-Trihydroxy-2-piperidinomethylisoflavoneYield 92.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4',5,7-Trihydroxy-2-bromomethylisoflavone (160 mg) was dissolved in 2 ml, N,N-dimethylformamide, 100 mg piperidine was added to the solution, and the mixture was stirred at room temperature for three hours. The solvent was distilled off under reduced pressure, the residue was purified by silca gel column chromatography (chlorofrom: methanol=96:4), and the solid thus obtained was recrystallized from ethanol, giving 150 mg of 4',5,7-trihydroxy-2-piperidinomethylisoflavone.

Workup

  1. additionwas added to the solution
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silca gel column chromatography (chlorofrom: methanol=96:4)
  4. customthe solid thus obtained
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-6426d959283d415cb7e47ca62f70afff
Source dataset
uspto-grants-1989_06
Patent number
US04841077

Reaction notes

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