Sodium Hydroxide → (E)-1-[3-(4-hydroxy-3-methoxyphenyl)-2-propenyl]-4-(4-phenoxyphenyl)piperidine

HRID 992365Notes

Reaction equation

HRID 992365 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=O)=[CH:4][C:3]=1[O:31][CH3:32].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[CH2:10][N:12]2[CH2:17][CH2:16][CH:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:4][C:3]=1[O:31][CH3:32]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 18412170(E)-1-[3-(4-hydroxy-3-methoxyphenyl)-1-oxo-2-propenyl]-4(4-phenoxyphenyl)piperidineHCID 21226445Aluminium lithium hydride

Product 1

HCID 18412177(E)-1-[3-(4-hydroxy-3-methoxyphenyl)-2-propenyl]-4-(4-phenoxyphenyl)piperidineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an 8 ml tetrahydrofuran solution of 400 mg of the compound (5) synthesized in Reference Example 5 was added under ice cooling 60 mg of lithium aluminum hydride, then the resulting mixture was stirred at room temperature for two hours. A 10% aqueous solution of sodium hydroxide solution was added, then the product was extracted with methylene chloride. The extract was dried, filtered, then concentrated under reduced pressure to obtain a residue which was then purified by silica gel column chromatography (methylene chloride:methanol=20:1) to obtain the above-referenced compound (19) in an amount of 273 mg (yield 72%).

Workup

  1. extractionthe product was extracted with methylene chloride
  2. customThe extract was dried
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a residue which
  6. customwas then purified by silica gel column chromatography (methylene chloride:methanol=20:1)

Sources & evidence

ORD record
ord-aa6c553b7ead4941b1dd5c2ef3812286
Source dataset
uspto-grants-2002_10
Patent number
US06469010B1

Reaction notes

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