Methyl iodide → 4-[3-[3-[2-(1-Adamantyl)ethyl]-3-pentylureido]propyl]-1-methylpyridinium iodide

HRID 1393169Notes

Reaction equation

HRID 1393169 reaction equation
[CH3:1][I:2].[C:3]12([CH2:13][CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:16]([NH:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[CH:24][CH:23]=3)=[O:17])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2>CC(C)=O>[I-:2].[C:3]12([CH2:13][CH2:14][N:15]([CH2:28][CH2:29][CH2:30][CH2:31][CH3:32])[C:16](=[O:17])[NH:18][CH2:19][CH2:20][CH2:21][C:22]3[CH:23]=[CH:24][N+:25]([CH3:1])=[CH:26][CH:27]=3)[CH2:4][CH:5]3[CH2:6][CH:7]([CH2:8][CH:9]([CH2:11]3)[CH2:10]1)[CH2:12]2

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 101585621-(2-(1-Adamantyl)ethyl)-1-pentyl-3-(3-(4-pyridyl)propyl)urea

Product 1

HCID 219740454-[3-[3-[2-(1-Adamantyl)ethyl]-3-pentylureido]propyl]-1-methylpyridinium iodideYield 96%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Methyl iodide (90 μl, 1.5 mmol) was added to a solution of 1-[2-(1-adamantyl)ethyl]-1-pentyl-3-[3-(4-pyridyl)propyl]urea (Compound No. 1-1) (0.30 g, 0.73 mmol) in acetone (1.5 ml) at room temperature, and the mixture was stirred overnight. The solvent was evaporated under reduced pressure from the reaction mixture, and the precipitated crystals were filtered off with ethyl acetate to give 389 mg (96%) of the titled compound.

Workup

  1. customThe solvent was evaporated under reduced pressure from the reaction mixture
  2. filtrationthe precipitated crystals were filtered off with ethyl acetate

Sources & evidence

ORD record
ord-ea005508f0de46448393d9578996475f
Source dataset
uspto-grants-2008_03
Patent number
US07345064B2

Reaction notes

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