Reaktion #67176

ord-919a95f3ce0743c4b8b1e4f48a275598

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
C1CCNCC1
piperidine
→
CS(=O)(=O)c1ccc2c(c1)OC(CN1CCCCC1)CO2
1-{[7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]METHYL}PIPERIDINE

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
C1CCNCC1
piperidine

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 MeOH/Et2O

Vorschrift

A mixture of [7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.6 g, 1.5 mmol), piperidine (1 ml) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on SCX-3 column (TEA/MeOH) and by flash chromatography through a small plug of silica (DCM/MeOH, 5:95). Yield: 0.4 g, 85%. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 248° C. MS m/z (rel. intensity, 70 eV) 311 (M+, 1), 310 (M+, 2), 207 (3), 99 (7), 98 (bp).

Quelle

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