Iodoethane → HCID 53682906, compound

HRID 374223Notes

Reaction equation

HRID 374223 reaction equation
Cl.[CH2:2]1[O:31][C:30]2[C:4](=[CH:5][C:6]3[O:11][CH2:10][C@H:9]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]4[CH:28]=[CH:27][C:21]5[CH:22]=[CH:23][C:24](=[O:26])[O:25][C:20]=5[CH:19]=4)[O:8][C:7]=3[CH:29]=2)[O:3]1.I[CH2:33][CH3:34].C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH2:2]1[O:31][C:30]2[C:4](=[CH:5][C:6]3[O:11][CH2:10][C@H:9]([CH2:12][N:13]([CH2:33][CH3:34])[CH2:14][CH2:15][CH2:16][O:17][C:18]4[CH:28]=[CH:27][C:21]5[CH:22]=[CH:23][C:24](=[O:26])[O:25][C:20]=5[CH:19]=4)[O:8][C:7]=3[CH:29]=2)[O:3]1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 86746374(S)-7-[3-[[(2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride

Product 1

HCID 53682906HCID 53682906, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(S)-7-[3-[[(2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride (0.60 g, 1.3 mmole), iodoethane (0.16 ml, 2.0 mmole) and diisopropylethylamine (2.26 ml, 13.0 mmole) were combined in 50 ml of DMF and heated at 60° C. for 2 days under a nitrogen atmosphere. The solvent was then removed in vacuum and the residue was dissolved in dichloromethane and washed with an equal volume of aqueous saturated sodium bicarbonate. The aqueous portion was back-extracted with dichloromethane and the combined organic portions were washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was chromatographed on a silica gel column using dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum, and the residue redissolved in methanol and acidified with 4N HCl/isopropanol to pH<3 in an ice bath. The mixture was diluted with isopropanol to precipitate a white solid, which was recrystallized from methanol to give 0.25 g of the title compound as the monohydrochloride, m.p. 209° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washwashed with an equal volume of aqueous saturated sodium bicarbonate
  4. extractionThe aqueous portion was back-extracted with dichloromethane
  5. washthe combined organic portions were washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed on a silica gel column
  10. concentrationconcentrated in vacuum
  11. dissolutionthe residue redissolved in methanol
  12. customacidified with 4N HCl/isopropanol to pH<3 in an ice bath
  13. additionThe mixture was diluted with isopropanol
  14. customto precipitate a white solid, which
  15. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-7e21ffc617b44d77be76df3710948a19
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

Loading…