HCID 14986021, compound → HCID 14986022, compound

HRID 2051478Notes

Reaction equation

HRID 2051478 reaction equation
[N:1]1([C:7]2[C:8]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C:21]3=[O:26])=[N:9][C:10]3[C:15]([C:16]=2[N+:17]([O-])=O)=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>O1CCCC1.[Pd]>[NH2:17][C:16]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]=[C:8]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][C:21]2=[O:26])[C:7]=1[N:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 14986021HCID 14986021, compound

Product 1

HCID 14986022HCID 14986022, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

The 3-piperidino-4-nitro-2-(2'-oxocyclohexyl)quinoline (8.5 g, 0.024 mol) was dissolved in tetrahydrofuran (50 ml) and subjected to reduction in the presence of 10g palladium-on-carbon (1.2 g). After completion of the reaction, the palladium-on-carbon catalyst was filtered off and the mother liquor was concentrated. Following purification by chromatography on an alumina column using chloroform as a developing solvent, recrystallization from ethanol was conducted to obtain 4-amino-3-piperidino-2-(2'-oxocyclohexyl)quinoline in an amount of 6.1 g (yield, 74%).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe palladium-on-carbon catalyst was filtered off
  3. concentrationthe mother liquor was concentrated
  4. custompurification by chromatography on an alumina column
  5. customas a developing solvent, recrystallization from ethanol

Sources & evidence

ORD record
ord-b998930aaea140898dcaffd9a6e69245
Source dataset
uspto-grants-1991_05
Patent number
US05019574

Reaction notes

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