Sodium Iodide → HCID 19778678, compound

HRID 374219Notes

Reaction equation

HRID 374219 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][NH2:12])[O:7][C:6]=2[CH:13]=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>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][NH:12][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)[O:7][C:6]=2[CH:13]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 197786897-Chloro-2,3-dihydro-1,4-benzodioxin-2-methanamine

Product 1

HCID 19778678HCID 19778678, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-Dihydro-7-chloro-1,4-benzodioxin-2-methanamine (1.72 g, 8.62 mmole), 7-(3-chloropropoxy)coumarin (1.88 g, 7.88 mmole), diisopropylethylamine (7.5 ml, 43.1 mmole) and sodium iodide (1.37 g, 9.14 mmole) were combined in 200 ml of DMF and heated at 80°-100° C. for 3 days under a nitrogen atmosphere. The solvent was then removed in vacuum and the residue was column chromatographed on silica gel using first 0.5% methanol/dichloromethane and then 1% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum, during which procedure the free base began to come out of solution. This material was collected by filtration and recrystallized from isopropanol with addition of 4N HCl/isopropanol to give 0.27 g of white solid, monohydrochloride, m.p. 235°-242° C.

Workup

  1. temperatureheated at 80°-100° C. for 3 days under a nitrogen atmosphere
  2. customThe solvent was then removed in vacuum
  3. customchromatographed on silica gel using first 0.5% methanol/dichloromethane
  4. concentrationconcentrated in vacuum, during which procedure the free base
  5. filtrationThis material was collected by filtration
  6. customrecrystallized from isopropanol with addition of 4N HCl/isopropanol

Sources & evidence

ORD record
ord-4a69efc494784eaf886d303b600445c8
Source dataset
uspto-grants-1992_11
Patent number
US05166367

Reaction notes

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