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

HRID 1375180Notes

Reaction equation

HRID 1375180 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.Cl.O.[NH:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.[OH-].[K+].O>CO>[NH:12]1[CH2:13][CH:14]=[C:15]([C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][CH:2]=2)[CH2:16][CH2:17]1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 14797Potassium HydroxideHCID 2723901Piperonylamine

Product 1

HCID 27610233-(1,2,3,6-Tetrahydropyridin-4-yl)-1H-indoleYield 87.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of indole (1.01 g, 8.59 mmol), 4-piperidone monohydrate hydrochloride (1.99 g, 12.9 mmol) and KOH (1.74 g, 31 mmol) in CH3OH (9 mL) was heated to reflux for 21 h. After cooling the reaction mixture to room temperature, H2O (14 mL) was added. The suspension was filtered, the solid was washed with (1:1) MeOH:H2O (20 mL) and air-dried to give 1.49 g (87%) of the title compound as an off-white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 21 h
  3. filtrationThe suspension was filtered
  4. washthe solid was washed with (1:1) MeOH
  5. dry with materialH2O (20 mL) and air-dried

Sources & evidence

ORD record
ord-0726920006e1403c8e457fa8e9eea07e
Source dataset
uspto-grants-2007_01
Patent number
US07166723B2

Reaction notes

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