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

HRID 11465Notes

Reaction equation

HRID 11465 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-b337c3f6b67740aa913be31c3193b3a0
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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