4-(4-Fluoro-benzyl)-piperidine → [4-(4-fluorobenzyl)piperidine-1-yl]-(6-hydroxy-1H-indole-2-yl)-methanone

HRID 896437Notes

Reaction equation

HRID 896437 reaction equation
[F:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:24]=[C:23]2[C:19]([CH:20]=[C:21]([C:25](O)=[O:26])[NH:22]2)=[CH:18][CH:17]=1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:25]([C:21]3[NH:22][C:23]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[C:16]([OH:15])[CH:24]=4)=[O:26])[CH2:11][CH2:12]2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 36998414-(4-Fluoro-benzyl)-piperidineHCID 223501916-Hydroxy-1H-indole-2-carboxylic acid

Product 1

HCID 9903141[4-(4-fluorobenzyl)piperidine-1-yl]-(6-hydroxy-1H-indole-2-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared from 4-(4-fluorobenzyl)piperidine [J. Med. Chem., 35, 4903. (1992)] and 6-hydroxy-1H-indole-2-carboxylic acid in acetonitrile at room temperature. The reaction mixture is concentrated and the residue is purified by column chromatography using Kiesel gel 60 as adsorbent (Merck) and toluene:methanol=4:1 as eluent. Mp.: 180-182° C. (toluene).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. customthe residue is purified by column chromatography

Sources & evidence

ORD record
ord-152a78daf10f44dfafd0b82ea650b8ed
Source dataset
uspto-grants-2005_07
Patent number
US06919355B2

Reaction notes

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