Hydrochloric Acid → HCID 13084715, compound

HRID 1462553Notes

Reaction equation

HRID 1462553 reaction equation
ON1C2C(=CC=CC=2)C([CH:13]([N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH2:14][CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)CC1=O.Cl.[H][H].[OH-:32].[Na+]>O1CCOCC1.[Pd].CCOCC>[C:17]1([N:26]2[CH2:25][CH2:24][N:23]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]3[CH:18]=[C:19]4[C:20](=[CH:21][CH:22]=3)[NH:23][C:13](=[O:32])[CH2:14][CH2:15]4)[CH2:28][CH2:27]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 131713562HCID 131713562, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13084715HCID 13084715, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

1.57 Grams of 6-[1-hydroxy-4-(4-phenyl-1-piperazinyl-butyl]-3,4-dihydrocarbostyril and 0.2 g of palladium black were suspended in 100 ml of dioxane, then 10 ml of concentrated hydrochloric acid was added thereto and the mixture was catalytically hydrogenated under 1.5-3.0 kg/cm2 of hydrogen gas at 80°-90° C. The catalyst was removed by filtration and the filtrate was dried under a reduced pressure. To the residue thus obtained were added 10N-NaOH and ether and the mixture was stirred at a room temperature for 30 mintues. The crystals formed were collected by filtration and separated by a silica-gel chromatography, then recrystallized from isopropanol-diisopropyl ether to obtain 6-[4-(4-phenyl-1-piperazinyl)butyl]-3,4-dihydro-carbostyril. Yield: 0.60 g (40%). Colorless prism-like crystals. Melting point: 151°-152° C.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was dried under a reduced pressure
  3. customTo the residue thus obtained
  4. customThe crystals formed
  5. filtrationwere collected by filtration
  6. customseparated by a silica-gel chromatography
  7. customrecrystallized from isopropanol-diisopropyl ether

Sources & evidence

ORD record
ord-ba9236b5eb424077a38064fb356f9e42
Source dataset
uspto-grants-1984_07
Patent number
US04460593

Reaction notes

Loading…