HCID 70047877, compound → HCID 19086852, compound

HRID 1464615Notes

Reaction equation

HRID 1464615 reaction equation
[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[C:14]([C:21]([N+:24]([O-])=O)=[CH:22][CH:23]=2)[CH:15]=[CH:16][C:17](OC)=[O:18])[CH2:8][CH2:7]1)=[O:4].[H][H]>C(O)C.[C].[Pd]>[CH3:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:13]=[C:14]3[C:21](=[CH:22][CH:23]=2)[NH:24][C:17](=[O:18])[CH2:16][CH2:15]3)[CH2:8][CH2:7]1)=[O:4]

Participants

5

Reactant 2

HCID 70047877HCID 70047877, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19086852HCID 19086852, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

1.25 Grams of methyl 3-[4-(N-methylacetylamino)1-piperidyl]-6-nitrocinnamate was dissolved in 50 ml of ethanol, then 0.4 g of 10%-palladium carbon was added thereto, the reaction mixture was stirred until the absorption of hydrogen gas was stopped under conditions of at room temperature and normal pressure. The catalyst was removed by filtration, the filtrate was concentrated by evaporating the solvent, the residue thus obtained was purified by means of a silica gel column chrmatography (eluent: dichloromethane:methanol=50:1), then recrystallized from methanol-diethyl ether to yield 0.82 g of 6-[4-(N-methylacetylamino)-1-piperidyl]-3,4-dihydrocarbostyril. Light yellow needle-like crystals. Melting point: 195°-197° C.

Workup

  1. customwas stopped under conditions of at room temperature and normal pressure
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customby evaporating the solvent
  5. customthe residue thus obtained
  6. customwas purified by means of a silica gel column chrmatography (eluent: dichloromethane:methanol=50:1)
  7. customrecrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-13ce6e2f63794e37aa5607f8f45de65a
Source dataset
uspto-grants-1994_04
Patent number
US05306719

Reaction notes

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