Methyl iodide → HCID 19809532, compound

HRID 374220Notes

Reaction equation

HRID 374220 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([CH2:13][NH:14][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:29]=[CH:28][C:22]4[CH:23]=[CH:24][C:25](=[O:27])[O:26][C:21]=4[CH:20]=3)[O:9][C:8]=2[CH:30]=1.CI.[CH:33](N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][CH:10]([CH2:13][N:14]([CH3:33])[CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:29]=[CH:28][C:22]4[CH:23]=[CH:24][C:25](=[O:27])[O:26][C:21]=4[CH:20]=3)[O:9][C:8]=2[CH:30]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 81531DiisopropylethylamineHCID 19778667HCID 19778667, compound

Product 1

HCID 19809532HCID 19809532, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

7-[3-[[(2,3-Dihydro-7-methoxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride (2.2 g, 5.0 mmole) was dissolved in 100 ml of DMF and 700 mg (5.0 mmole) of methyl iodide added, followed by 2.6 g (20 mmole) of diisopropylethylamine. The mixture was heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with 300 ml of dichloromethane. The mixture was washed with 300 ml portions of saturated aqueous sodium bicarbonate, saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography on 100 g of silica gel using chloroform as eluant and crystallized from isopropanol with addition of 2.5 ml of 4N isopropanolic HCl to give 0.20 g of the title compound as a monohydrochloride, m.p. 176°-178° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. washThe mixture was washed with 300 ml portions of saturated aqueous sodium bicarbonate, saturated sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customThe residue was purified by column chromatography on 100 g of silica gel
  7. customcrystallized from isopropanol with addition of 2.5 ml of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-a4f7ec101ad8449bbf35d4d19e10ad81
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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