Iodoethane → HCID 53856076, compound

HRID 374227Notes

Reaction equation

HRID 374227 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C@H:9]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:28]=[CH:27][C:21]4[CH:22]=[CH:23][C:24](=[O:26])[O:25][C:20]=4[CH:19]=3)[O:8][C:7]=2[CH:29]=1.[CH:30](N(C(C)C)CC)(C)[CH3:31].ICC>CN(C=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C@H:9]([CH2:12][N:13]([CH2:30][CH3:31])[CH2:14][CH2:15][CH2:16][O:17][C:18]3[CH:28]=[CH:27][C:21]4[CH:22]=[CH:23][C:24](=[O:26])[O:25][C:20]=4[CH:19]=3)[O:8][C:7]=2[CH:29]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 81531DiisopropylethylamineHCID 88427992HCID 88427992, compound

Product 1

HCID 53856076HCID 53856076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

(S)-7-[3-[[(2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-yl)methyl]amino]propoxy]-2H-1-benzopyran-2-one hydrochloride (0.89 g, 2.13 mmole), diisopropylethylamine (0.80 ml, 4.59 mmole) and iodoethane (0.24 ml, 3.0 mmole) were combined in DMF and heated at 60° C. for 15 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with 75 ml ofdichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue (1.82 g) was column chromatographed on 75 g of silica gel using first 0.5% methanol/dichloromethane and then 2% methanol/dichloromethane as eluant. The product-containing fractions were concentrated in vacuum and the free base redissolved in methanol. 2.8 ml of 4N isopropanolic HCl was added, the mixture was brought to a boil on a hot plate and the solvent gradually replaced with isopropanol. Upon cooling, 0.66 g of the title compound precipitated as a yellow solid, monohydrochloride, quarter hydrate, m.p. 204°-207° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on 75 g of silica gel using first 0.5% methanol/dichloromethane
  7. concentrationThe product-containing fractions were concentrated in vacuum
  8. dissolutionthe free base redissolved in methanol
  9. addition2.8 ml of 4N isopropanolic HCl was added
  10. temperatureUpon cooling
  11. custom0.66 g of the title compound precipitated as a yellow solid, monohydrochloride, quarter hydrate, m.p. 204°-207° C.

Sources & evidence

ORD record
ord-4c81cd303e2c408b8cca0d57fdd3b343
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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