Dimethylformamide → 3-[[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]ethylamino]propoxyl-2H-1-benzopyran-2-one

HRID 374228Notes

Reaction equation

HRID 374228 reaction equation
[CH2:1]([NH:3][CH2:4][CH:5]1[O:10][C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6]1)[CH3:2].BrCCCO[C:20]1[CH:29]=[C:28]2[C:23]([CH:24]=[CH:25][C:26](=[O:30])[O:27]2)=[CH:22][CH:21]=1.C(N([CH:37]([CH3:39])C)CC)(C)C.CN([CH:43]=[O:44])C>>[O:10]1[C:9]2[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=2[O:7][CH2:6][CH:5]1[CH2:4][N:3]([CH2:37][CH3:39])[CH2:1][CH2:2][CH2:43][O:44][C:25]1[C:26](=[O:30])[O:27][C:28]2[CH:29]=[CH:20][CH:21]=[CH:22][C:23]=2[CH:24]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 30614N-Ethyl-2,3-dihydro-1,4-benzodioxin-2-methanamineHCID 81531DiisopropylethylamineHCID 27571767-(3-bromopropoxy)-2H-chromen-2-one

Product 1

HCID 867463753-[[(2,3-Dihydro-1,4-benzodioxin-2-yl)methyl]ethylamino]propoxyl-2H-1-benzopyran-2-one

Conditions

Temperature
76 °C

Procedure

N-Ethyl-2,3-dihydro-1,4-benzodioxin-2-methanamine (4.67 g, 24.2 mmole), 7-(3-bromopropoxy)coumarin (6.92 g, 24.4 mmole), and diisopropylethylamine (6.70 ml, 38.5 mmole) were combined in 300 ml of DMF and heated at 76° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue (10 g) was column chromatographed on 225 g of silica gel using 40% ethyl acetate/dichloromethane as eluant. The product-containing fractions were concentrated in vacuum and the residue crystallized from isopropanol with the addition of 30 ml of 4N isopropanolic HCl to give 4.94 g of the title compound as a white solid, monohydrochloride, m.p. 147°-152° 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 225 g of silica gel using 40% ethyl acetate/dichloromethane as eluant
  7. concentrationThe product-containing fractions were concentrated in vacuum
  8. customthe residue crystallized from isopropanol with the addition of 30 ml of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-9d3a2665dc6e43e8a41a8848147d1e03
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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