Hydrochloric Acid → 1-(4-Methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-methylidene-2,3-dihydro-1-benzofuran-5-yl)piperazine

HRID 2063812Notes

Reaction equation

HRID 2063812 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:17]([CH3:31])=[C:18]([CH3:30])[C:19]4[O:23][C:22]([CH3:25])([CH3:24])[C:21]([CH3:27])(O)[C:20]=4[C:28]=3[CH3:29])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1>C(#N)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[C:17]([CH3:31])=[C:18]([CH3:30])[C:19]4[O:23][C:22]([CH3:24])([CH3:25])[C:21](=[CH2:27])[C:20]=4[C:28]=3[CH3:29])[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 229356081-(2,2,3,4,6,7-Hexamethyl-3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine

Product 1

HCID 229355751-(4-Methoxyphenyl)-4-(2,2,4,6,7-pentamethyl-3-methylidene-2,3-dihydro-1-benzofuran-5-yl)piperazineYield 92.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

10% hydrochloric acid (5 mL) was added to a suspension of acetonitrile (15 mL) containing 5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,3,4,6,7-hexamethyl-2,3-dihydro-1-benzofuran-3-ol (1.70 g, 4.14 mmol) obtained in Reference Example 105, and the mixture was stirred at room temperature for 6 hours. The reaction solution was concentrated under reduced pressure, and after that, 10% potassium carbonate aqueous solution was added to the residue so that the aqueous layer became alkaline. Then, extraction was performed using ethyl acetate. The organic layer was washed with water and saturated saline, and then dried using anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the obtained residue was crystallized using ethanol to give 1.50 g of the title compound (yield: 92%)

Workup

  1. customobtained in Reference Example 105
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionafter that, 10% potassium carbonate aqueous solution was added to the residue so that the aqueous layer
  4. extractionThen, extraction
  5. washThe organic layer was washed with water and saturated saline
  6. customdried
  7. customThe solvent was removed under reduced pressure
  8. customthe obtained residue was crystallized

Sources & evidence

ORD record
ord-a184c4090b73473fa7a648037186c6fc
Source dataset
uspto-grants-2012_10
Patent number
US08288390B2

Reaction notes

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