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Hydrochloric Acid → HCID 59484992, compound

HRID 2063926
Notes
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Reaction equation

HRID 2063926 reaction equation
CO[C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:30])=[C:17]([CH3:29])[C:18]4[O:22][C:21]([CH2:24]C#N)([CH3:23])[CH2:20][C:19]=4[C:27]=3[CH3:28])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[OH-:31].[Na+].[CH2:33](O)C.Cl.[C:37]([O:40]CC)(=[O:39])C>O>[CH3:33][O:31][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[CH2:10][CH2:11][N:12]([C:15]3[C:16]([CH3:30])=[C:17]([CH3:29])[C:18]4[O:22][C:21]([CH2:24][C:37]([OH:40])=[O:39])([CH3:23])[CH2:20][C:19]=4[C:27]=3[CH3:28])[CH2:13][CH2:14]2)=[CH:7][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 59485094HCID 59485094, compound

Product 1

HCID 59484992HCID 59484992, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of {5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}acetonitrile (260 mg, 0.641 mmol) synthesized in Example 140, 8N sodium hydroxide aqueous solution (2.0 mL) and ethanol (10 mL) was stirred under heated reflux for 15 hours. After cooled to room temperature, 1N hydrochloric acid (16 mL) was added thereto, and the reaction solution was distributed using water and ethyl acetate. The organic layer was washed with saturated saline and dried using anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 90:10-70:30) and crystallized from ethyl acetate-hexane to obtain 150 mg of the title compound (yield 55%). Melting point was 171 to 174° C. (decomposition).

Workup

  1. temperatureunder heated
  2. temperaturereflux for 15 hours
  3. washThe organic layer was washed with saturated saline
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel chromatography (hexane-ethyl acetate 90:10-70:30)
  7. customcrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-99225ffb40f54db79765a2b5d8791eec
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08288390B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes