Sodium Iodide → N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-2-amine

HRID 452397Notes

Reaction equation

HRID 452397 reaction equation
Cl[CH2:2][CH:3]1[O:8][C:7]2[CH:9]=[C:10]([S:13]([CH3:16])(=[O:15])=[O:14])[CH:11]=[CH:12][C:6]=2[CH2:5][O:4]1.[CH3:17][CH:18]([NH2:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>C(#N)C>[CH3:16][S:13]([C:10]1[CH:11]=[CH:12][C:6]2[CH2:5][O:4][CH:3]([CH2:2][NH:20][CH:18]([CH3:19])[CH3:17])[O:8][C:7]=2[CH:9]=1)(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6363IsopropylamineHCID 11430Potassium CarbonateHCID 668873282-(chloromethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine

Product 1

HCID 44481358N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-2-amineYield 56.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(chloromethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine (0.1 g, 0.38 mmol), propan-2-amine (1.30 ml, 152 mmol), potassium carbonate (80 mg, 0.57 mmol), some few crystals of sodium iodide in ACN (3 ml) was heated in a micro wave oven at 170° C. for 40 min. After cooling to ambient temperature the volatiles were evaporated in vacuum. The oily residue was chromatographed twice on a silica column with EtOAc/MeOH (7:1) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded the title compound (61 mg, 55%). MS m/z (rel. intensity, 70 eV) 285 (M+, 1), 123 (11), 86 (15), 77 (16), 72 (bp).

Workup

  1. customwere evaporated in vacuum
  2. customThe oily residue was chromatographed twice on a silica column with EtOAc/MeOH (7:1) as eluent
  3. customCollection of the fractions
  4. additioncontaining pure
  5. customproduct and evaporation of the solvent

Sources & evidence

ORD record
ord-572d120304614b96b18f338366d6326a
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

Loading…