Phenethyl tosylate → 5-Methoxy-7-methyl-3-(1-methylpiperdin-4-yl)-1-phenethyl-1H-indole

HRID 1766235Notes

Reaction equation

HRID 1766235 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:13]1[CH2:18][CH2:17][N:16]([CH3:19])[CH2:15][CH2:14]1.[H-].[K+].[CH2:22](OS(C1C=CC(C)=CC=1)(=O)=O)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C1OCCOCCOCCOCCOCCOC1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[C:10]([CH3:12])[CH:11]=1)[N:8]([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:7]=[C:6]2[CH:13]1[CH2:14][CH2:15][N:16]([CH3:19])[CH2:17][CH2:18]1

Participants

5

Reactant 4

HCID 20522Phenethyl tosylate2×HCID 2855718-Crown-6HCID 82127Potassium hydrideHCID 179800985-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole

Product 1

HCID 694351515-Methoxy-7-methyl-3-(1-methylpiperdin-4-yl)-1-phenethyl-1H-indoleYield 15%

Procedure

By a method similar to Preparation 26, using 5-methoxy-7-methyl-3-(1-methylpiperidin-4-yl)-1H-indole (5.81 mmol, 1.50 g), 35% potassium hydride (5.81 mmol, 0.665 g), toluene-4-sulfonic acid phenethyl ester (5.81 mmole, 1.60 g), additional 18-crown-6 (5.22 mmol,1.38 g) and additional toluene-4-sulfonic acid phenethyl ester (2.90 mmole, 0.802 g) were added to afford 0.31 g (15%) of the title compound: mass spectrum (ion spray): m/z=363 (M+1).

Workup

  1. customBy a method similar to Preparation 26
  2. additionwere added

Sources & evidence

ORD record
ord-e408eb65c2814b97ad9e3bd205567392
Source dataset
uspto-grants-2007_06
Patent number
US07230011B2

Reaction notes

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