HCID 59485041, compound → HCID 59485088, compound

HRID 1850497Notes

Reaction equation

HRID 1850497 reaction equation
[CH2:1]([N:8](C)[CH2:9][C:10]1([CH3:36])[CH2:14][C:13]2[C:15]([CH3:35])=[C:16]([N:21]3[CH2:26][CH2:25][N:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=4)[CH2:23][CH2:22]3)[C:17]([CH3:20])=[C:18]([CH3:19])[C:12]=2[O:11]1)C1C=CC=CC=1>[C].[Pd].C(OCC)(=O)C>[CH3:34][O:33][C:30]1[CH:29]=[CH:28][C:27]([N:24]2[CH2:23][CH2:22][N:21]([C:16]3[C:17]([CH3:20])=[C:18]([CH3:19])[C:12]4[O:11][C:10]([CH2:9][NH:8][CH3:1])([CH3:36])[CH2:14][C:13]=4[C:15]=3[CH3:35])[CH2:26][CH2:25]2)=[CH:32][CH:31]=1

Participants

4

Reactant 1

HCID 59485041HCID 59485041, compound

Product 1

HCID 59485088HCID 59485088, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To the ethyl acetate (6 mL) solution of N-benzyl-1-{5-[4-(4-methoxyphenyl)piperazin-1-yl]-2,4,6,7-tetramethyl-2,3-dihydro-1-benzofuran-2-yl}-N-methylmethaneamine (190 mg, 0.380 mmol) synthesized in Example 103, 10%-palladium carbon (comprising 50% moisture, 70 mg) was added, and then the mixture was stirred at room temperature for 15 hours under hydrogen atmosphere. The reaction mixture was filtered to remove the palladium carbon, and the filtrate was concentrated under reduced pressure. The residue was purified by basic silica gel chromatography (hexane-ethyl acetate 95:5-50:50), and recrystallized from ethyl acetate-hexane to obtain the title compound 50 mg (yield 32%). Melting point was 107 to 113° C. (ethyl acetate-hexane).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the palladium carbon
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by basic silica gel chromatography (hexane-ethyl acetate 95:5-50:50)
  5. customrecrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-455a9c54d3324be69a428cc4cf0b0e1d
Source dataset
uspto-grants-2015_02
Patent number
US08957069B2

Reaction notes

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