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

HRID 2357496Notes

Reaction equation

HRID 2357496 reaction equation
[OH-].[K+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.Cl.[NH:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.O>CO>[NH:13]1[CH2:14][CH:15]=[C:16]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[NH:3][CH:4]=2)[CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 798IndoleHCID 962WaterHCID 14797Potassium HydroxideHCID 30848514-Piperidone hydrochloride

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

KOH (8.19 g, 146 mmole), indole (3.87 g, 33 mmole) and piperidine-4-one hydrochloride (10.22 g, 85.7 mmole) were suspended in methanol (50 ml) and heated for 8 hours at 65° C. under argon. Water (50 ml) was added dropwise at RT to the mixture over a period of 40 minutes. The solid thereby formed was filtered off, washed with water (3×20 ml) and recrystallised from methanol (20 ml). 3-(1,2,3,6-tetrahydropyridine-4-yl)-1H-indole was obtained in a yield of 4.26 g (71%) as a yellow solid with an m.p. of 172°-174° C.

Workup

  1. customThe solid thereby formed
  2. filtrationwas filtered off
  3. washwashed with water (3×20 ml)
  4. customrecrystallised from methanol (20 ml)

Sources & evidence

ORD record
ord-19174c58c20c4596afa7534d300121bc
Source dataset
uspto-grants-2010_07
Patent number
US07759385B2

Reaction notes

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