Reaktion #67187

ord-341ef346f78544b5bb5f23988f960d7b

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OCC2COc3c(F)cc(S(C)(=O)=O)cc3O2)cc1
[5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine
→
CCNCC1COc2c(F)cc(S(C)(=O)=O)cc2O1
N-{[5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}ETHANAMINE

Edukte

Cc1ccc(S(=O)(=O)OCC2COc3c(F)cc(S(C)(=O)=O)cc3O2)cc1
[5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine

Reagenzien

Keine

Lösungsmittel

CC#N
ACN

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification on SCX-3 column (TEA/MeOH)
  2. 2
    Sonstigecrystallized from EtOH

Vorschrift

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).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524766B2uspto-grants-2013_09