Hydrochloric Acid → HCID 66759872, compound

HRID 1850396Notes

Reaction equation

HRID 1850396 reaction equation
Cl.C(O)C.COC[O:8][C:9]1[C:17]2[O:16][C:15]([CH3:19])([CH3:18])[C:14](=[O:20])[C:13]=2[C:12]([CH3:21])=[C:11]([N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[C:10]=1[CH3:36].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[OH:8][C:9]1[C:17]2[O:16][C:15]([CH3:18])([CH3:19])[C:14](=[O:20])[C:13]=2[C:12]([CH3:21])=[C:11]([N:22]2[CH2:27][CH2:26][N:25]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[CH2:24][CH2:23]2)[C:10]=1[CH3:36]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702EthanolHCID 66760694HCID 66760694, compoundHCID 86585896Sodium bicarbonate water

Product 1

HCID 66759872HCID 66759872, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Concentrated hydrochloric acid (0.1 mL) was added to a solution of ethanol (16 mL) containing 7-(methoxymethoxy)-5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6-tetramethyl-1-benzofuran-3(2H)-one (800 mg, 1.82 mmol) synthesized in Reference Example 72 and the mixture was stirred under heated reflux for 24 hours. After that, concentrated hydrochloric acid (0.1 mL) was further added thereto, and the mixture was stirred under heated reflux for 24 hours. The reaction solution was cooled to room temperature and poured into saturated sodium bicarbonate water, and extraction was performed using ethyl acetate. The extract was washed with saturated saline, and dried using anhydrous magnesium sulfate, followed by concentration under reduced pressure. The residue was crystallized using ethyl acetate and hexane to give 630 mg of the title compound (yield: 87%).

Workup

  1. customsynthesized in Reference Example 72
  2. temperatureunder heated
  3. temperaturereflux for 24 hours
  4. stirringthe mixture was stirred
  5. temperatureunder heated
  6. temperaturereflux for 24 hours
  7. washThe extract was washed with saturated saline
  8. customdried
  9. concentrationfollowed by concentration under reduced pressure
  10. customThe residue was crystallized

Sources & evidence

ORD record
ord-db81189ce37846c598133a20f7817535
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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