Reaktion #2186200

ord-9b60706dc5304f028f75a7ab89725982

Reaktionsgleichung

O=c1oc2cc(N3CCNCC3)ccc2cc1-c1nc2ccccc2s1
3-benzothiazol-2-yl-7-piperazin-1-yl-chromen-2-one
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
OCCI
2-iodoethanol
O=c1oc2cc(N3CCN(CCO)CC3)ccc2cc1-c1nc2ccccc2s1
desired product
Ausbeute 26.0%
O=c1oc2cc(N3CCN(CCO)CC3)ccc2cc1-c1nc2ccccc2s1
3-Benzothiazol-2-yl-7-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-chromen-2-one
Ausbeute 26.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    ExtraktionThe reaction mixture is extracted with ethyl acetate
  2. 2
    Waschena saturated solution of sodium carbonate and washed with brine
  3. 3
    TrocknenThe combined organic phases are dried with sodium sulphate
  4. 4
    Sonstigeevaporated
  5. 5
    Sonstigechromatographed (silica gel, dichloromethane/methanol 95:5+1% conc. NH4OH)

Vorschrift

240 mg crude 3-benzothiazol-2-yl-7-piperazin-1-yl-chromen-2-one in 10 mL DMF are stirred for 72 h at room temperature in the presence of 858 mg (at least 4 eq.) cesium carbonate and 0.103 mL (at least 2 eq.) 2-iodoethanol. The reaction mixture is extracted with ethyl acetate and a saturated solution of sodium carbonate and washed with brine. The combined organic phases are dried with sodium sulphate and evaporated. The residue is column chromatographed (silica gel, dichloromethane/methanol 95:5+1% conc. NH4OH) to yield 70 mg (26%) desired product as an orange solid.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07569337B2uspto-grants-2009_08