Piperidine → HCID 19603257, compound

HRID 1604594Notes

Reaction equation

HRID 1604594 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([OH:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([CH3:13])[CH:3]=1.[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([CH3:13])[CH:3]=[C:2]2[N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 8082PiperidineHCID 122197224-Chloro-8-hydroxy-2-methylquinoline

Product 1

HCID 19603257HCID 19603257, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

The mixture of 4-chloro-8-hydroxy-2-methylquinoline 600 mg), piperidine (6.13 ml) and tetrabutylammonium iodide (10 mg) was refluxed for 18 hours. The cooled reaction mixture was concentrated in vacuo and to the residue was added chloroform and aqueous sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and evaporated in vacuo. The residue was recrystallized from n-hexane to give 8-hydroxy-2-methyl-4-piperidinoquinoline (712 mg) as pale brown crystals.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe cooled reaction mixture
  3. concentrationwas concentrated in vacuo and to the residue
  4. additionwas added chloroform and aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from n-hexane

Sources & evidence

ORD record
ord-09d1cada42f340588466542cc80a9720
Source dataset
uspto-grants-1999_11
Patent number
US05994368

Reaction notes

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