Isopropyl iodide → N-(Propan-2-yl)-2H-1,3-benzodioxol-5-amine

HRID 991504Notes

Reaction equation

HRID 991504 reaction equation
[CH2:1]1[O:10][C:9]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=2[O:2]1.I[CH:12]([CH3:14])[CH3:13].C(N(CC)CC)C>CO>[CH:12]([NH:6][C:5]1[CH:7]=[CH:8][C:9]2[O:10][CH2:1][O:2][C:3]=2[CH:4]=1)([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 8471TriethylamineHCID 843101,3-Benzodioxol-5-amine

Product 1

HCID 12789466N-(Propan-2-yl)-2H-1,3-benzodioxol-5-amineYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4-(methylenedioxy)aniline (9.0 g), and 2-iodopropane (5.9 ml) in methanol (100 mL) was added triethylamine (8.2 mL). The mixture was refluxed for 50 h, and then concentrated in vacuo. The residue was taken with 1:1 hexane/EtOA (180 mL), washed with water and brine, dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by chromatography (3:1 hexane/EtOAc) to yield the title compound as an oil (10.1 g, 85%). 1H NMR (CDCl3): 6.64 (d, J=8.3, 1H), 6.23 (d, J=2.2, 1H), 6.03 (dd, J=2.2, 8.3, 1H), 5.85 (s, 2H), 3.51 (m, 1H), 3.19 (br s, 1H), 1.18 (d, J=6.1, 6H).

Workup

  1. temperatureThe mixture was refluxed for 50 h
  2. concentrationconcentrated in vacuo
  3. washwashed with water and brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography (3:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-49d03e49bd194edc9818ddb7ddc365a9
Source dataset
uspto-grants-2002_10
Patent number
US06465472B1

Reaction notes

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