Hydroquinone → 1-[2-(4-Cyanophenyl)ethyl]-4-(4-hydroxyphenoxymethyl)piperidin-4-ol

HRID 967764Notes

Reaction equation

HRID 967764 reaction equation
[H-].[Na+].CN(C)C=O.[C:8]1([CH:15]=[CH:14][C:12]([OH:13])=[CH:11][CH:10]=1)[OH:9].[C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][N:26]2[CH2:33][CH2:32][C:29]3([CH2:31][O:30]3)[CH2:28][CH2:27]2)=[CH:20][CH:19]=1)#[N:17]>O>[C:16]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][N:26]2[CH2:33][CH2:32][C:29]([CH2:31][O:9][C:8]3[CH:15]=[CH:14][C:12]([OH:13])=[CH:11][CH:10]=3)([OH:30])[CH2:28][CH2:27]2)=[CH:22][CH:23]=1)#[N:17]

Participants

6

Reactant 4

HCID 785HydroquinoneHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 858197211-[2-(4-Cyanophenyl)ethyl]piperidin-4-spiro-2'-oxirane

Product 1

HCID 102916131-[2-(4-Cyanophenyl)ethyl]-4-(4-hydroxyphenoxymethyl)piperidin-4-olYield 9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

60% sodium hydride (46 mg) was added to an anhydrous dimethylformamide solution (4 mL) of hydroquinone (0.18 g) under cooling with ice-water and the mixture was stirred at room temperature for fourty minutes under nitrogen atmosphere. The compound (0.40 g) obtained in Step 3 was added to the mixture, and the reaction mixture was stirred at 80° C. for four hours under nitrogen atmosphere. Water (40 mL) was added to the mixture under cooling with ice-water and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine successively, dried over anhydrous sodium sulfate and then, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol=49:1 to 19:1) and the obtained fractions were concentrated and washed with ether-ethyl acetate to obtain the titled compound (52 mg).

Workup

  1. stirringthe reaction mixture was stirred at 80° C. for four hours under nitrogen atmosphere
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (eluent; ethyl acetate:methanol=49:1 to 19:1)
  7. concentrationthe obtained fractions were concentrated
  8. washwashed with ether-ethyl acetate

Sources & evidence

ORD record
ord-007219dae42345aa8a5a0c8ad874fdf1
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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