Sodium Iodide → 7-[3-[[(2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-yl)methyl]ethylamino]propoxy]-2H-1-benzopyran-2-one

HRID 2082467Notes

Reaction equation

HRID 2082467 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]1[O:10][C:9]2[CH:11]=[C:12]([OH:15])[CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)[CH3:2].Cl[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][C:27](=[O:31])[O:28]2)=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[OH:15][C:12]1[CH:13]=[CH:14][C:8]2[O:7][CH2:6][CH:5]([CH2:4][N:3]([CH2:1][CH3:2])[CH2:17][CH2:18][CH2:19][O:20][C:21]3[CH:22]=[CH:23][C:24]4[CH:25]=[CH:26][C:27](=[O:31])[O:28][C:29]=4[CH:30]=3)[O:10][C:9]=2[CH:11]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 19778687N-Ethyl-2,3-dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine

Product 1

HCID 197786647-[3-[[(2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-yl)methyl]ethylamino]propoxy]-2H-1-benzopyran-2-oneYield 13.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
94 °C

Procedure

N-Ethyl-2,3-dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine (2.11 g, 13.1 mmole), 7-(3-chloropropoxy)coumarin (3.44 g, 14.4 mmole), diisopropylethylamine (11 ml, 63.2 mmole) and sodium iodide (1.98 g, 13.2 mmole) were combined in 175 ml of DMF and heated at 94° C. for 2 days under a nitrogen atmosphere. The solvent was then removed in vacuum and the residue column chromatographed on silica gel using first 0.5% methanol/dichloromethane and then 1.5% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue redissolved in dichloromethane and boiled on a hot plate, the dichloromethane gradually being replaced with isopropanol. 4N HCl/isopropanol (4 ml) was added and the title compound was collected by filtration. A second recrystallization from isopropanol yielded 0.73 g of white solid, monohydrochloride, m.p. 208°-215° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. customthe residue column chromatographed on silica gel using first 0.5% methanol/dichloromethane
  3. concentrationconcentrated in vacuum
  4. dissolutionthe residue redissolved in dichloromethane
  5. addition4N HCl/isopropanol (4 ml) was added
  6. filtrationthe title compound was collected by filtration
  7. customA second recrystallization from isopropanol

Sources & evidence

ORD record
ord-0b2d4ea816b947609d6a4297e9ec3c87
Source dataset
uspto-grants-1993_02
Patent number
US05189171

Reaction notes

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