1-(3-Cyclohexylidene-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine hydrochloride → 1-(3-Cyclohexyl-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

HRID 1272305Notes

Reaction equation

HRID 1272305 reaction equation
Cl.[C:2]1(=[C:8]2[C:12]3[C:13]([CH3:33])=[C:14]([N:19]4[CH2:24][CH2:23][N:22]([C:25]5[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=5)[CH2:21][CH2:20]4)[C:15]([CH3:18])=[C:16]([CH3:17])[C:11]=3[O:10][C:9]2([CH3:35])[CH3:34])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1>C(O)C.CO.[C].[Pd]>[CH:2]1([CH:8]2[C:12]3[C:13]([CH3:33])=[C:14]([N:19]4[CH2:20][CH2:21][N:22]([C:25]5[CH:26]=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=5)[CH2:23][CH2:24]4)[C:15]([CH3:18])=[C:16]([CH3:17])[C:11]=3[O:10][C:9]2([CH3:35])[CH3:34])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 1

HCID 229355891-(3-Cyclohexylidene-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine hydrochloride

Product 1

HCID 102765001-(3-Cyclohexyl-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazineYield 26%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 1-(3-cyclohexylidene-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine hydrochloride obtained in Example 45 (390 mg, 0.79 mmol), 10% palladium-carbon (300 mg) in ethanol (10 ml) and methanol (10 ml) was stirred at room temperature under hydrogen pressure of 4–5 atmospheres for 8 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was diluted with 10% aqueous potassium carbonate, and the aqueous layer was made alkaline and extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (hexane/ethyl acetate=20/1) to obtain 95 mg (yield 26%) of the title compound via recrystallization (ethanol). mp. 119–121° C.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionThe residue was diluted with 10% aqueous potassium carbonate
  4. extractionextracted with ethyl acetate
  5. extractionThe organic extract
  6. washwas washed with water and saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with silica gel column chromatography (hexane/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-12458ed1a89542b89249a47b8a853cd7
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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