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

HRID 452454Notes

Reaction equation

HRID 452454 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][CH3:17])[O:10][C:9]=2[CH:18]=1)(=[O:4])=[O:3].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>CCOC(C)=O>[CH2:19]([N:15]([CH2:14][CH:11]1[O:10][C:9]2[CH:18]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=[CH:7][C:8]=2[CH2:13][O:12]1)[CH2:16][CH3:17])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 44481361N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}ethanamine

Product 1

HCID 67155941(+)-N-benzyl-N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}ethanamineYield 89.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-{[7-(methylsulfonyl)-4H-1,3-benzodioxin-2-yl]methyl}ethanamine (0.93 g, 3.4 mmol), benzylbromide (0.43 ml, 3.6 mmol), potassium carbonate (0.61 g, 4.4 mmol) and ACN (20 ml) were heated at 70° C. for 2 h. EtOAc (50 ml) was added before the reaction mixture was filtered and concentrated. Purification by flash chromatography (isooctane/EtOAc 1:1) afforded the title compound (1.1 g). 1H-NMR (400 MHz, MeOH): δ 7.47 (1H, dd, J1 8 Hz, J2 1.6 Hz), δ 7.31 (7H, m), δ 5.18 (1H, t, J 5.2 Hz), δ 4.97 (2H, dd, J1 41 Hz, J2 15 Hz), δ 3.09 (3H, s), δ 2.90 (2H, m), δ 2.70 (2H, m), δ 1.12 (3H, t, J 7.2 Hz).

Workup

  1. filtrationwas filtered
  2. concentrationconcentrated
  3. customPurification by flash chromatography (isooctane/EtOAc 1:1)

Sources & evidence

ORD record
ord-2924dbc0e9c74d178076a9f79b4dee1c
Source dataset
uspto-grants-2013_07
Patent number
US08492372B2

Reaction notes

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