Tetrahydrofuran → HCID 59526929, compound

HRID 384488Notes

Reaction equation

HRID 384488 reaction equation
C([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=[C:11](/[CH:19]=[CH:20]/[CH:21]2[CH2:26][CH2:25][N:24](C(OCC3C=CC=CC=3)=O)[CH2:23][CH2:22]2)[C:10]=1[CH3:37])C1C=CC=CC=1.C1COCC1>[Pd].C(O)C>[CH3:37][C:10]1[C:9](=[O:8])[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[NH:12][C:11]=1[CH2:19][CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 59527482HCID 59527482, compound

Product 1

HCID 59526929HCID 59526929, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a mixture of benzyl 4-{(E)-2-[4-(benzyloxy)-3-methylquinolin-2-yl]vinyl}piperidine-1-carboxylate (978 mg), THF (6 mL) and ethanol (6 mL) was added 10% palladium-activated carbon (200 mg) under nitrogen atmosphere. The mixture was stirred at room temperature under hydrogen atmosphere of 3 atms, for 4 hours. The catalyst was removed by filtration, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Fuji Silysia Chemical Ltd., NH, eluent: chloroform/methanol=97/3˜92/8), and the solvent was evaporated. The residue was washed with ether, and collected by filtration to obtain 3-methyl-2-(2-piperidin-4-ylethyl)quinolin-4(1H)-one (490 mg).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified by silica gel column chromatography (Fuji Silysia Chemical Ltd., NH, eluent: chloroform/methanol=97/3˜92/8)
  4. customthe solvent was evaporated
  5. washThe residue was washed with ether
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0e31651bd28549f39fc64e84771c7f04
Source dataset
uspto-grants-2013_02
Patent number
US08367702B2

Reaction notes

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