Indole → 3-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

HRID 2222277Notes

Reaction equation

HRID 2222277 reaction equation
C[O-].[Na+].[NH:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.O.Cl>CO>[NH:13]1[CH2:14][CH:15]=[C:16]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[NH:4][CH:5]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 798IndoleHCID 337214-PiperidoneHCID 10942334Sodium MethoxideHCID 21885828Hydrate;hydrochloride

Product 1

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of sodium methoxide (450 ml, 30% in methanol, 2.5 mol) in 1000 ml of methanol was added indole (50 g, 0.427 mol) and 4-piperidone.H2O.HCl (162 g, 1.05 mol). The mixture was heated under reflux for 18 h forming a yellow precipitate. The mixture was concentrated and water (1000 ml) was added. The precipitate was collected, washed with water and petroleum ether and then dried in a vacuum oven at 50° C. Yield 77 g (91%) of a pale yellow solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 h
  3. customforming a yellow precipitate
  4. concentrationThe mixture was concentrated
  5. additionwater (1000 ml) was added
  6. customThe precipitate was collected
  7. washwashed with water and petroleum ether
  8. customdried in a vacuum oven at 50° C

Sources & evidence

ORD record
ord-bcf11618979d455d99ab61862a7df2ce
Source dataset
uspto-grants-2008_05
Patent number
US07371769B2

Reaction notes

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