HCID 23359081, compound → HCID 23359105, compound

HRID 232716Notes

Reaction equation

HRID 232716 reaction equation
[CH3:1][N:2]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:22]=[C:21]([O:29]CC3C=CC=CC=3)[CH:20]=2)=[O:18])[CH2:13][CH2:12]1)[CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[H][H]>C(O)C.[C].[Pd]>[CH3:1][N:2]([CH:11]1[CH2:16][CH2:15][N:14]([C:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][C:21](=[O:29])[CH:20]=2)=[O:18])[CH2:13][CH2:12]1)[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 23359081HCID 23359081, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23359105HCID 23359105, compoundYield 3.4%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

150 mg of 10% palladium-carbon was added to 11 g of 4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinyl}carbonyl-2-benzyloxyquinoline (obtained in Reference Example 2) in 20 ml of ethanol. The mixture was stirred at room temperature at a hydrogen pressure of 1 atm. for 1 hour. The reaction mixture was filtered to remove the catalyst. The filtrate was concentrated under reduced pressure. The residue was crystallized from diethyl ether and then re- crystallized from ligroin-ethyl acetate to obtain 0.3 g of 4-{4-[N-methyl-N-(2-phenylethyl)amino]-1-piperidinyl}carbonylcarbostyril as a white powder having a melting point of 155°-158° C.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was crystallized from diethyl ether
  5. customre- crystallized from ligroin-ethyl acetate

Sources & evidence

ORD record
ord-9c707bb21f724dccb10fc773056dd174
Source dataset
uspto-grants-1997_01
Patent number
US05591751

Reaction notes

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