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

HRID 1272283Notes

Reaction equation

HRID 1272283 reaction equation
Cl.[CH3:2][C:3]1([CH3:31])[C:7]([CH3:9])(O)[C:6]2[C:10]([CH3:30])=[C:11]([N:16]3[CH2:21][CH2:20][N:19]([C:22]4[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=4)[CH2:18][CH2:17]3)[C:12]([CH3:15])=[C:13]([CH3:14])[C:5]=2[O:4]1>C(#N)C>[CH3:29][O:28][C:25]1[CH:24]=[CH:23][C:22]([N:19]2[CH2:20][CH2:21][N:16]([C:11]3[C:12]([CH3:15])=[C:13]([CH3:14])[C:5]4[O:4][C:3]([CH3:2])([CH3:31])[C:7](=[CH2:9])[C:6]=4[C:10]=3[CH3:30])[CH2:17][CH2:18]2)=[CH:27][CH:26]=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

A solution of 10% hydrochloric acid (5 ml) was added to a solution of 1-(2,2,3,4,6,7-hexamethyl-3-hydroxy-2,3-dihydro-1-benzofuran-5-yl)-4-(4-methoxyphenyl)piperazine (1.70 g, 4.14 mmol) obtained in Reference Example 26 in acetonitrile (15 ml) at room temperature and the mixture was stirred for 6 hours. The resulting mixture was concentrated under reduced pressure, and the residue was made to basic with 10% aqueous potassium carbonate. The aqueous layer was extracted with ethyl acetate. The organic extract was washed with water and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was crystallized from ethanol to obtain 1.50 g (yield 92%) of the title compound. mp. 134–136° C.

Workup

  1. concentrationThe resulting mixture was concentrated under reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. extractionThe organic extract
  4. washwas washed with water and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was crystallized from ethanol

Sources & evidence

ORD record
ord-f16357ccae1d470687c2d1756f9a2d5c
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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