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

HRID 2075900Notes

Reaction equation

HRID 2075900 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-7be8d36626d94a5d841a6681ac6b42cf
Source dataset
uspto-grants-2011_04
Patent number
US07923461B2

Reaction notes

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