2-Aminomethyl-1,4-benzodioxane → HCID 17751566, compound

HRID 2363225Notes

Reaction equation

HRID 2363225 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH2:12].[S:13](N)([NH2:16])(=[O:15])=[O:14]>O1CCOCC1>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH:12][S:13]([NH2:16])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 150532-Aminomethyl-1,4-benzodioxaneHCID 82267Sulfamide

Product 1

HCID 17751566HCID 17751566, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (4.4 g, 26 mmol) and sulfamide (5.1 g, 53 mmol) were combined in 1,4 dioxane (100 mL) and refluxed for 2 h. The reaction was cooled to room temperature and a small amount of solid was filtered and discarded. The filtrate was evaporated in vacuo and the residue was purified using flash column chromatography (DCM:Methanol—10:1) to yield a white solid. The solid was recrystallized from DCM to yield the title compound as a white solid.

Workup

  1. temperaturerefluxed for 2 h
  2. filtrationa small amount of solid was filtered
  3. customThe filtrate was evaporated in vacuo
  4. customthe residue was purified
  5. customto yield a white solid
  6. customThe solid was recrystallized from DCM

Sources & evidence

ORD record
ord-8b54066fa1574d5a9c3ea52626104be9
Source dataset
uspto-grants-2014_04
Patent number
US08691867B2

Reaction notes

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