Sodium Iodide → N-[3-(Quinolin-7-yloxy)propyl]-2,3-dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine

HRID 2254302

Reaction equation

HRID 2254302 reaction equation
[CH2:1]1[O:15][C:14]2[C:3](=[CH:4][C:5]3[O:10][CH2:9][CH:8]([CH2:11][NH2:12])[O:7][C:6]=3[CH:13]=2)[O:2]1.Br[CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:30]=[C:29]2[C:24]([CH:25]=[CH:26][CH:27]=[N:28]2)=[CH:23][CH:22]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[N:28]1[C:29]2[C:24](=[CH:23][CH:22]=[C:21]([O:20][CH2:19][CH2:18][CH2:17][NH:12][CH2:11][CH:8]3[O:7][C:6]4[CH:13]=[C:14]5[O:15][CH2:1][O:2][C:3]5=[CH:4][C:5]=4[O:10][CH2:9]3)[CH:30]=2)[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 197450147-(3-Bromopropoxy)quinolineHCID 197450172,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine

Product 1

HCID 9930518N-[3-(Quinolin-7-yloxy)propyl]-2,3-dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamineYield 57.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2,3-Dihydro-6,7-methylenedioxy-1,4-benzodioxin-2-methanamine (1.3 g, 6.2 mmole), 7-(3-bromopropoxy)quinoline (1.53 g, 5.5 mmole), diisopropylethylamine 2.6 g, 20 mmole) and sodium iodide (5.5 g, 37 mmole) were combined in 200 ml of DMF and heated at 80° C. for 15 hours under a nitrogen atmosphere. The solvent was then removed in vacuum and replaced with 500 ml of dichloromethane. The mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on 250 g of silica gel using 3% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the residue (2.25 g) recrystallized from ethanol with the addition of 6 ml of 4N isopropanolic HCl to give 1.25 g of the title compound as a yellow solid dihydrochloride salt, m.p. 224°-226° C.

Workup

  1. customThe solvent was then removed in vacuum
  2. washThe mixture was washed with 250 ml each of saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on 250 g of silica gel using 3% methanol/dichloromethane as eluant
  7. concentrationconcentrated in vacuum
  8. customthe residue (2.25 g) recrystallized from ethanol with the addition of 6 ml of 4N isopropanolic HCl

Sources & evidence

ORD record
ord-1f3b8dd37368441c944a3642b06276fb
Source dataset
uspto-grants-1993_08
Patent number
US05235055

Linked notes

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