Methyl iodide → HCID 58080349, compound

HRID 1751802Notes

Reaction equation

HRID 1751802 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 in the form of an oil. Analytical HPLC-MS (method A): RT=1.65 min.

Workup

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

Sources & evidence

ORD record
ord-8668ac42d52e4ddc811cb8a230409b5f
Source dataset
uspto-grants-2015_10
Patent number
US09161927B2

Reaction notes

Loading…