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

HRID 452394Notes

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]([NH2:20])[CH2:18][CH3:19]>CCO>[CH3:16][S:13]([C:10]1[CH:11]=[CH:12][C:6]2[CH2:5][O:4][CH:3]([CH2:2][NH:20][CH2:17][CH2:18][CH3:19])[O:8][C:7]=2[CH:9]=1)(=[O:15])=[O:14]

Participants

Conditions

Temperature: 140 °C

Procedure

A mixture of 2-(bromomethyl)-7-(methylsulfonyl)-4H-1,3-benzodioxine (0.50 g, 1.63 mmol), propan-1-amine (2.0 ml, 24.3 mmol), EtOH (3.0 ml) was heated in a micro wave oven at 140° C. for 30 min. The mixture was evaporated to dryness. The residue was chromathographed on a silica column using EtOAc:MeOH (5:1) as eluent, affording the title compound as a light-yellow solid (0.56 g). The product was washed with several portions of ethyl acetate to give a pure white powder as the title compound (0.43 g, 90%). 0.24 g of the title compound was converted into the hydrochloric acid salt and crystallized from EtOH/DEE. M.p. 213° C. MS m/z (rel. intensity, 70 eV) 285 (M+, 1), 123 (10), 77 (15), 72 (bp), 51 (12).

Workup

customThe mixture was evaporated to dryness

Sources & evidence

ORD record: ord-4e3b09f734b245658d4d373007768ec1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492372B2

Reaction notes

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