Sodium Iodide → HCID 54110178, compound

HRID 374222Notes

Reaction equation

HRID 374222 reaction equation
Cl.[CH2:2]1[O:16][C:15]2[C:4](=[CH:5][C:6]3[O:11][CH2:10][C@H:9]([CH2:12][NH2:13])[O:8][C:7]=3[CH:14]=2)[O:3]1.Cl[CH2:18][CH2:19][CH2:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([CH:26]=[CH:27][C:28](=[O:32])[O:29]2)=[CH:24][CH:23]=1.[I-].[Na+]>CN(C=O)C>[CH2:2]1[O:16][C:15]2[C:4](=[CH:5][C:6]3[O:11][CH2:10][C@H:9]([CH2:12][NH:13][CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:23]=[CH:24][C:25]5[CH:26]=[CH:27][C:28](=[O:32])[O:29][C:30]=5[CH:31]=4)[O:8][C:7]=3[CH:14]=2)[O:3]1

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 67796344HCID 67796344, compound

Product 1

HCID 54110178HCID 54110178, compoundYield 16.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

(S)-2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine hydrochloride (5.50 g, 22.4 mmole), 7-(3-chloropropoxy)coumarin (5.49 g, 23.0 mmole) diisopropylethylamine (39.0 ml, 224 mmol) and sodium iodide (3.45 g, 23.0 mmole) were combined in 200 ml of DMF and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with chloroform. The mixture was treated with an equal volume of saturated aqueous sodium bicarbonate and the aqueous phase was then back-extracted with 3:1 chloroform-isopropanol. The combined organic extracts were washed with water, dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum. The residue was chromatographed on a silica gel column using dichloromethane as eluant. The product-containing fractions (Rf=0.59 on silica gel tlc with 1:5:95 ammonium hydroxide-methanol-chloroform) 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 to precipitate a white solid. This was recrystallized from methanol and triturated with a small amount of isopropanol to give 1.50 g of the title compound as an off-white crystalline, solid, monohydrochloride, m.p. 244°-245° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. additionThe mixture was treated with an equal volume of saturated aqueous sodium bicarbonate
  3. extractionthe aqueous phase was then back-extracted with 3:1 chloroform-isopropanol
  4. washThe combined organic extracts were washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customThe residue was chromatographed on a silica gel column
  9. concentrationconcentrated in vacuum
  10. dissolutionthe residue redissolved in methanol
  11. customacidified with 4N HCl/isopropanol to pH<3 in an ice bath
  12. customto precipitate a white solid
  13. customThis was recrystallized from methanol
  14. customtriturated with a small amount of isopropanol

Sources & evidence

ORD record
ord-118f4b9630b74b388f7db15521eeaa44
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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