Hydrochloric Acid → 3-(Piperidin-4-yl)quinolin-2(1H)-one

HRID 1699243Notes

Reaction equation

HRID 1699243 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[C:8](=[O:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:3][CH:2]=1.Cl.[H][H]>[Pd].C(O)C>[NH:1]1[CH2:2][CH2:3][CH:4]([C:7]2[C:8](=[O:17])[NH:9][C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:5][CH2:6]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 18321205HCID 18321205, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 183210463-(Piperidin-4-yl)quinolin-2(1H)-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 8.6 g (0.0387 mol) of 3-(4-pyridinyl)-2(1H)-quinolone, 1.2 1 of ethanol, 39 ml (0.039 mol) of 1N hydrochloric acid and 8.0 g of 10% palladium/charcoal was hydrogenated at a temperature of 40° C. until about 0.08 mol of hydrogen had been taken up. The mixture was freed from catalyst, the filtrate was evaporated down in vacuo, the residue was taken up in 200 ml of water and made ammoniacal. Common salt was added up to saturation point and the mixture was continuously extracted with dichloromethane using a perforator. The dichloromethane phase was evaporated down, the residue remaining was separated from by-products by chromatography over silica gel using FM1 as eluant. The appropriate fractions were combined, freed from solvent, dissolved in a little isopropanol and converted with ethanolic hydrogen chloride solution into the hydrochloride. Colourless crystals. Yield: 2.68 g (26.2% of theory).

Workup

  1. customthe filtrate was evaporated down in vacuo
  2. additionCommon salt was added up to saturation point
  3. extractionthe mixture was continuously extracted with dichloromethane using a perforator
  4. customThe dichloromethane phase was evaporated down
  5. customthe residue remaining was separated from by-products by chromatography over silica gel using FM1 as eluant
  6. dissolutiondissolved in a little isopropanol

Sources & evidence

ORD record
ord-9f2b3cc0587a49a28eca02dc91fa65ec
Source dataset
uspto-grants-2002_02
Patent number
US06344449B1

Reaction notes

Loading…