1-Benzyl-4-piperidone → 2-benzyl-3,4-dihydro-1H-benzo[b][1,6]naphthyridine

HRID 1597273Notes

Reaction equation

HRID 1597273 reaction equation
[OH-].[K+].C(O)C.[NH2:6][C:7]1[CH:14]=[CH:13][CH:12]=[CH:11][C:8]=1[CH:9]=O.[CH2:15]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:15]([N:22]1[CH2:27][CH2:26][C:25]2[N:6]=[C:7]3[CH:14]=[CH:13][CH:12]=[CH:11][C:8]3=[CH:9][C:24]=2[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 192201-Benzyl-4-piperidoneHCID 682552-AminobenzaldehydeHCID 21946426Potassium hydroxide ethanol

Product 1

HCID 38452462-benzyl-3,4-dihydro-1H-benzo[b][1,6]naphthyridineYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10% potassium hydroxide/ethanol solution (120 ml) was added dropwise to a solution of 2-aminobenzaldehyde (26 g, 0.21 mol) and 1-benzyl-4-piperidone (40 g, 0.21 mol) in absolute ethanol (430 ml) over a period of 1 hour. After stirring overnight, the reaction solution was concentrated under reduced pressure and extracted with ethyl acetate, and the extract solution was washed with water and then dried over anhydrous sodium sulfate. The organic solvent was removed by concentration under reduced pressure, and the residue was recrystallized from ethyl acetate-isopropyl ether to obtain the desired compound (37 g, 63%) as white crystals.

Workup

  1. concentrationthe reaction solution was concentrated under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washthe extract solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe organic solvent was removed by concentration under reduced pressure
  6. customthe residue was recrystallized from ethyl acetate-isopropyl ether

Sources & evidence

ORD record
ord-e9c507f0ef8c4825aed59c3badac9a7e
Source dataset
uspto-grants-2001_09
Patent number
US06294547B1

Reaction notes

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