Sodium Iodide → HCID 53909604, compound

HRID 374216Notes

Reaction equation

HRID 374216 reaction equation
[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C@H:7]([CH2:10][NH2:11])[CH2:8][O:9][C:4]=2[CH:3]=1.Cl[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25](=[O:29])[O:26]2)=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[OH:1][C:2]1[CH:13]=[CH:12][C:5]2[O:6][C@H:7]([CH2:10][NH:11][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[CH:23]=[CH:24][C:25](=[O:29])[O:26][C:27]=4[CH:28]=3)[CH2:8][O:9][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 54083613HCID 54083613, compound

Product 1

HCID 53909604HCID 53909604, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
94 °C

Procedure

(R)-2,3-Dihydro-6-hydroxy-1,4-benzodioxin-2-methanamine (2.58 g, 14.2 mmole), 7-(3-chloropropoxy)coumarin (3.08 g, 12.9 mmole), diisopropylethylamine (10 ml, 57 mmole) and sodium iodide (1.98 g, 13.2 mmole) were combined in 175 ml of DMF and heated at 94° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum. The residue was twice column chromatographed on silica gel using 1% methanol/dichloromethane as eluant. The product-containing fractions (Rf=0.45 on silica gel with 5% methanol/dichloromethane) were combined and concentrated in vacuum and the pure free base redissolved in methanol and boiled on a hot plate, the methanol gradually being replaced with isopropanol. 4N HCL/isopropanol was added and the title compound was collected by filtration. After two additional recrystallizations from isopropanol, 0.35 g of white solid, monohydrochloride, m.p. 236°-242° C., was obtained.

Workup

  1. customThe solvent was then removed in vacuum
  2. customchromatographed on silica gel using 1% methanol/dichloromethane as eluant
  3. concentrationconcentrated in vacuum
  4. dissolutionthe pure free base redissolved in methanol
  5. addition4N HCL/isopropanol was added
  6. filtrationthe title compound was collected by filtration
  7. customAfter two additional recrystallizations from isopropanol, 0.35 g of white solid, monohydrochloride, m.p. 236°-242° C.
  8. customwas obtained

Sources & evidence

ORD record
ord-e6e6705e41ba44cf9511ea884ee1d8a5
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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