Ethylamine → N-{[5-Fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-YL]methyl}ethanamine

HRID 38909Notes

Reaction equation

CC1C=CC(S(O[CH2:12][CH:13]2[O:18][C:17]3[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[C:22]([F:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[CH2:28]([NH2:30])[CH3:29]>C(#N)C>[F:23][C:22]1[C:16]2[O:15][CH2:14][CH:13]([CH2:12][NH:30][CH2:28][CH3:29])[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.3 g, 0.8 mmol), ethanamine (1 ml, 70% in water) and ACN (2 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and on flash column chromatography (Isooctane/EtOAc/MeOH). Yield: 0.1 g, 61%. The amine was converted to the hydrochloric acid salt and crystallized from EtOH. M.p. 256° C. MS m/z (rel. intensity, 70 eV) 289 (M+, 12), 70 (17), 59 (20), 58 (bp), 56 (19).

Workup

customPurification on SCX-3 column (TEA/MeOH)
customcrystallized from EtOH

Sources & evidence

ORD record: ord-341ef346f78544b5bb5f23988f960d7b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

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