3-(4-Piperidinyl)-1H-indole → HCID 9908484, compound

HRID 1532622Notes

Reaction equation

HRID 1532622 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:15]1[CH2:20][CH2:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:1][CH:2]([OH:4])[CH2:3][N:15]1[CH2:20][CH2:19][CH:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:17][CH2:16]1)[CH:6]=[CH:7]2

Participants

3

Reactant 2

HCID 7022353-(4-Piperidinyl)-1H-indoleHCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indole

Product 1

HCID 9908484HCID 9908484, compoundYield 51%

Procedure

A methanolic solution of 1-N-glycidyl-5-fluoroindole (0.52 g, 3.0 mmole) from example 1 and 3-(4-piperidinyl)indole (0.6 g, 3.0 mmole) was refluxed under nitrogen for 15 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (ethyl acetate) to afford the titled compound as an oil (0.599 g, 50% yield). Treatment with a 0.25 M ethanolic solution of fumaric acid (0.5 equivalents) gave the required product as a white solid. The product was recrystallized twice from ethanol.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-33fc7a89a3cf4adf8eb53404b405dc76
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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