Triethylamine → HCID 17751567, compound

HRID 660410Notes

Reaction equation

HRID 660410 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].C(N(CC)CC)C.[CH3:20][N:21]([CH3:26])[S:22](Cl)(=[O:24])=[O:23]>CN(C=O)C>[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:22]([N:21]([CH3:26])[CH3:20])(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 150532-Aminomethyl-1,4-benzodioxaneHCID 83372Dimethylsulphamoyl chloride

Product 1

HCID 17751567HCID 17751567, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Racemic 2,3-dihydro-1,4-benzdioxin-2-ylmethylamine (8.25 g, 5.0 mmol) and triethylamine (1.52 g, 15 mmol) were combined in DMF (10 mL) and cooled in an ice bath as dimethylsulfamoyl chloride (1.44 g, 10 mmol) was added. The reaction mixture was then stirred for 3 hr with continued cooling. The reaction mixture was partitioned between ethyl acetate and water, and the ethyl acetate solution was washed with brine, dried (MgSO4) and evaporated in vacuo to yield an oil. The oil was purified using flash column chromatography (ethyl acetate:Heptane—1:1) to yield a white solid, which was recrystallized (ethyl acetate/Hexane) to yield the title compound as a white floccular solid.

Workup

  1. additionwas added
  2. customThe reaction mixture was partitioned between ethyl acetate and water
  3. washthe ethyl acetate solution was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo
  6. customto yield an oil
  7. customThe oil was purified
  8. customto yield a white solid, which
  9. customwas recrystallized (ethyl acetate/Hexane)

Sources & evidence

ORD record
ord-8cb57abc140342bd852b928eec83553c
Source dataset
uspto-grants-2011_12
Patent number
US08084490B2

Reaction notes

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