Methyl iodide → HCID 58080349, compound

HRID 405922Notes

Reaction equation

HRID 405922 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:2]1.[H-].[Na+].[CH3:25]I>CN(C)C=O>[CH3:25][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]2)=[CH:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22405349tert-Butyl 4-(1H-indol-3-yl)piperidine-1-carboxylate

Product 1

HCID 58080349HCID 58080349, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

500 mg tert-butyl 4-(1H-indol-3-yl)-piperidine-1-carboxylate are placed in 8 ml dimethylformamide and 73.3 mg sodium hydride (60% in mineral oil) are added. After 15 min 175 μl methyl iodide are added. The reaction mixture is stirred at ambient temperature. After the reaction is complete the product is purified directly by preparative HPLC (method C). 302 mg of the product are obtained as an oil.

Workup

  1. customis purified directly by preparative HPLC (method C)

Sources & evidence

ORD record
ord-839a03ed23024c19bfc0c49e2a4b7300
Source dataset
uspto-grants-2014_06
Patent number
US08754073B2

Reaction notes

Loading…