Ethylamine → N-{[7-(Methylsulfonyl)-4H-1,3-benzodioxin-2-YL]methyl}ethanamine
Reaction equation
Br[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.[CH2:17]([NH2:19])[CH3:18]>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:19][CH2:17][CH3:18])[O:8][C:7]=2[CH:9]=1)(=[O:15])=[O:14]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
A mixture of 2-(bromomethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine (0.40 g, 1.30 mmol), ethanamine (70% in water, 3.0 ml, 37.8 mmol) and ACN (3.0 ml) was heated in a microwave oven at 150° C. for 20 min. The volatiles were evaporated in vacuum. The residue was chromathographed twice on a silica column using EtOAc/MeOH (2:1) as eluent. Collection of the fractions containing pure product and evaporation of the solvent afforded the title compound (0.2 g, 57%). The amine was converted into hydrochloric acid salt and crystallized from EtOH/DEE (0.33 g). The salt was washed with several portions of DEE. M.p. 203° C. 1H-NMR (400 MHz, MeOH): δ 7.50 (1H, dd, J1 8, J2 1.6), δ 7.41 (1H, d, J 1.6), δ 7.31 (1H, d, J 8), δ 5.27 (1H, t, J 4.8), δ 5.04 (2H, dd, J1 49, J2 16), δ 3.11 (3H, s), δ 3.01 (2H, t, J 4.0), δ 2.77 (2H, q, J 6.8), δ 1.17 (3H, t, J 7.2).
Workup
- customThe volatiles were evaporated in vacuum
- customCollection of the fractions
- additioncontaining pure
- customproduct and evaporation of the solvent
Sources & evidence
- ORD record
- ord-43bbcf36e1a84ca7bf2e61a4e3019f25
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08492372B2
Reaction notes
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