Methyl iodide → HCID 10594839, compound

HRID 971058Notes

Reaction equation

HRID 971058 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4](=[O:24])[C:5]1[CH:10]=[CH:9][C:8]([C:11](=[C:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:7][CH:6]=1)[CH3:2].[C:27](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[CH2:25]([N:3]([CH2:1][CH3:2])[C:4](=[O:24])[C:5]1[CH:6]=[CH:7][C:8]([C:11](=[C:18]2[CH2:23][CH2:22][N:21]([CH3:27])[CH2:20][CH2:19]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:9][CH:10]=1)[CH3:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 9841259ARM390

Product 1

HCID 10594839HCID 10594839, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

N,N-Diethyl-4-[(piperidin-4-ylidene)-phenyl-methyl]-benzamide (0.34 g, 1.0 mmol) was disolved in acetonitrile (5 mL). Potassium carbonate (0.14 g, 1.0 mmol) and methyl iodide (63 μL, 1.0 mmol) was added with stirring at 25° C. After 30 min., the reaction mixture was evaporated and put onto silica gel for purification by chromatography using 0 to 10% MeOH(10% NH4OH) in CH2Cl2 to give 48 mg of the final product (28% of converted starting material), which was converted to the hydrochloride salt by treatment with HCl in ether.

Workup

  1. customthe reaction mixture was evaporated
  2. customput onto silica gel for purification by chromatography

Sources & evidence

ORD record
ord-ae354396a14c4fe1b10060730f2ee609
Source dataset
uspto-grants-2007_12
Patent number
US07312336B2

Reaction notes

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