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

HRID 1087963Notes

Reaction equation

HRID 1087963 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 silica gel column chromatography (chloroform:methanol=96:4), and the solid thus obtained was recrystallized from ethanol, giving 150 mg of 4',5,7-trihydroxy-2-piperidinomethylisoflavone.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (chloroform:methanol=96:4)
  3. customthe solid thus obtained
  4. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-a0facac0502545e8b8d6182de411615b
Source dataset
uspto-grants-1990_10
Patent number
US04960908

Reaction notes

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