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

HRID 2120991Notes

Reaction equation

HRID 2120991 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-5585e58c31ef431ea66b2c2ba385a350
Source dataset
uspto-grants-2004_02
Patent number
US06693197B2

Reaction notes

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