Reaktion #67174

ord-27bdb7f13fc74e059e3b537b3d00a4af

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OCC2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CCN
ethanamine
→
CCNCC1COc2ccc(S(C)(=O)=O)cc2O1
N-{[7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}ETHANAMINE

Edukte

Cc1ccc(S(=O)(=O)OCC2COc3ccc(S(C)(=O)=O)cc3O2)cc1
[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 flash column chromatography
  2. 2
    Sonstigewas crystallized from MeOH/Et2O

Vorschrift

A mixture of [7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.7 g, 1.8 mmol), ethanamine (1 ml, 70% in water) and ACN (3 ml) was heated under microwave radiation at 120° C. for 30 min. Purification on flash column chromatography and on SCX-3 column (TEA/MeOH). Yield: 0.4 g, 72%. The amine was converted to the hydrochloric acid salt and was crystallized from MeOH/Et2O. M.p. 261° C. MS m/z (rel. intensity, 70 eV) 271 (M+, 19), 226 (4), 207 (9), 79 (6), 58 (bp).

Quelle

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