Piperidine → 7,7-Dimethyl-5-oxo-2-piperidin-1-yl-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

HRID 1817816Notes

Reaction equation

HRID 1817816 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][C:10]2[N:9]=[C:8](SC)[C:7]([C:14]#[N:15])=[CH:6][C:5]=2[C:4](=[O:16])[CH2:3]1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(O)C>[CH3:1][C:2]1([CH3:17])[CH2:11][C:10]2[N:9]=[C:8]([N:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:7]([C:14]#[N:15])=[CH:6][C:5]=2[C:4](=[O:16])[CH2:3]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 31375507,7-Dimethyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile

Product 1

HCID 578831717,7-Dimethyl-5-oxo-2-piperidin-1-yl-5,6,7,8-tetrahydro-quinoline-3-carbonitrileYield 28.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 7,7-dimethyl-2-methylsulfanyl-5-oxo-5,6,7,8-tetrahydro-quinoline-3-carbonitrile (0.25 g, 1 mmol) and piperidine (0.32 ml, 4 mmol) in dry ethanol (3 ml) was stirred at reflux for 36 h. The reaction mixture was then evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (chloroform-methanol, 50:1) to give the title compound (0.08 g, 28%) as a colorless solid.

Workup

  1. temperatureat reflux for 36 h
  2. customThe reaction mixture was then evaporated under reduced pressure
  3. customThe residue was purified by flash chromatography on silica gel (chloroform-methanol, 50:1)

Sources & evidence

ORD record
ord-61ad601957ff441aa8913a521fedbe52
Source dataset
uspto-grants-2009_10
Patent number
US07598384B2

Reaction notes

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