Acetonitrile → (+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine

HRID 452449Notes

Reaction equation

HRID 452449 reaction equation
[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]2[CH2:13][O:12][CH:11]([CH2:14][NH:15][CH2:16][CH2:17][CH3:18])[O:10][C:9]=2[CH:19]=1)(=[O:4])=[O:3].[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOC(C)=O>[CH2:20]([N:15]([CH2:14][CH:11]1[O:10][C:9]2[CH:19]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[CH:7][C:8]=2[CH2:13][O:12]1)[CH2:16][CH2:17][CH3:18])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 44481357N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}propan-1-amine

Product 1

HCID 67155851(+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amineYield 76.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}propan-1-amine (1.2 g, 4.2 mmol), benzylbromide (0.53 ml, 4.4 mmol), potassium carbonate (0.70 g, 5.0 mmol) and ACN (50 ml) were heated at 60° C. for 2.5 h. EtOAc (100 ml) was added and the mixture was filtered and evaporated to dryness. Purification by flash chromatography (isooctane/EtOAc 1:1) and evaporation of pure fractions afforded the title compound (1.2 g). 1H-NMR (400 MHz, MeOH): δ 7.48 (1H, dd, J1 8.0 Hz, J2 2.0 Hz), δ 7.38-7.21 (7H, m), δ 5.18 (1H, t, J 5.6 Hz), δ 4.97 (2H, dd, J1 41.6 Hz, J2 15.6 Hz), δ 3.77 (2H, q, J 13.6 Hz), δ 3.10 (3H, s), δ 2.94-2.84 (2H, m), δ 2.58 (2H, dt, J1 7.2 Hz, J2 1.6 Hz), δ 1.56 (2H, m), δ 0.90 (2H, t, J 7.2 Hz).

Workup

  1. filtrationthe mixture was filtered
  2. customevaporated to dryness
  3. customPurification
  4. customby flash chromatography (isooctane/EtOAc 1:1) and evaporation of pure fractions

Sources & evidence

ORD record
ord-8e9b3f04055948dfbcece2f331c7a7f0
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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