Sodium Iodide → HCID 19778670, compound

HRID 2082458Notes

Reaction equation

HRID 2082458 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH:15]([CH2:18][NH2:19])[O:14][C:13]=2[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[CH:31][C:32](=[O:36])[O:33]2)=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][CH:15]([CH2:18][NH:19][CH2:22][CH2:23][CH2:24][O:25][C:26]4[CH:27]=[CH:28][C:29]5[CH:30]=[CH:31][C:32](=[O:36])[O:33][C:34]=5[CH:35]=4)[O:14][C:13]=3[CH:20]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 197786792,3-Dihydro-7-benzyloxy-1,4-benzodioxin-2-methanamine

Product 1

HCID 19778670HCID 19778670, compoundYield 25.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydro-7-benzyloxy-1,4-benzodioxin-2-methanamine (1.47 g, 5.42 mmole), 7-(3-chloropropoxy)coumarin (1.30 g, 5.45 mmole), diisopropylethylamine (4.0 ml, 23 mmole) and sodium iodide (4.17 g, 28 mmole) were combined in 150 ml of DMF and heated at 80°-100° C. for 2 days under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on silica gel using first dichloromethane, then 0.5% methanol/dichloromethane, and finally 1% methanol/dichloromethane as eluant. The fractions containing material with Rf=0.26 on silica gel tlc (2.5% methanol/chloroform) were combined and concentrated in vacuum and the residue crystallized from 50 ml of isopropanol with the addition of 4.0 ml of 4N isopropanolic HCl to give 0.66 g of title compound as an off-white solid, monohydrochloride, m.p. 179°-181° C.

Workup

  1. temperatureheated at 80°-100° C. for 2 days under a nitrogen atmosphere
  2. customThe solvent was then removed
  3. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel using first dichloromethane
  8. additionThe fractions containing material with Rf=0.26 on silica gel tlc (2.5% methanol/chloroform)
  9. concentrationconcentrated in vacuum
  10. customthe residue crystallized from 50 ml of isopropanol with the addition of 4.0 ml of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-a321a8b929fc4f89ab9d0ae6a042e93c
Source dataset
uspto-grants-1993_02
Patent number
US05189171

Reaction notes

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