Hydrochloric Acid → HCID 68707679, compound

HRID 2376311Notes

Reaction equation

HRID 2376311 reaction equation
C([NH:8][C:9]1[C:10]([CH3:28])=[C:11]([CH3:27])[C:12]2[O:16][C:15]([CH3:18])([CH3:17])[CH:14]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:13]=2[CH:26]=1)C1C=CC=CC=1.Cl>C(O)C.[C].[Pd]>[CH3:17][C:15]1([CH3:18])[CH:14]([C:19]2[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=2)[C:13]2[CH:26]=[C:9]([NH2:8])[C:10]([CH3:28])=[C:11]([CH3:27])[C:12]=2[O:16]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68708729HCID 68708729, compound

Product 1

HCID 68707679HCID 68707679, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-benzyl-2,2,6,7-tetramethyl-3-(4-methylphenyl)-2,3-dihydro-1-benzofuran-5-amine obtained in Reference Example 138 (6.60 g, 17.8 mmol) in ethanol (70 mL) was added 12 N hydrochloric acid (0.1 mL) and 10%—palladium carbon (hydrous 50%, 0.33 g), and the mixture was stirred under hydrogen condition of 5 atmosphere pressure at room temperature for 2 hours. The catalyst is filtered off, and the solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate, was washed with a saturated brine, and then was dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4) to obtain 4.42 g (yield 88%) of the title compound as an oily matter.

Workup

  1. filtrationThe catalyst is filtered off
  2. concentrationthe solution was concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwas washed with a saturated brine
  5. dry with materialwas dried over sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-589e8d8089b64e89bc586957f61cb12c
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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