Reaktion #660046

Reaktionsgleichung

(4-{3-[Benzothiazol-2-yl-(1-methyl-piperidin-4-yloxy)-methyl]-phenylsulfanyl}-butyl)-carbamic acid tert-butyl ester

oxalic acid

trifluoroacetic acid

→

oxalate

4-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}butylamine

Lösungsmittel

dichloromethane

acetone

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe mixture is evaporated to dryness
2. 2
   workup.ADDITIONby adding a solution of saturated sodium carbonate to pH 10
3. 3
   Extraktionthe aqueous phase is extracted with dichloromethane
4. 4
   TrocknenThe pooled organic extracts are dried over magnesium sulfate
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 90/10/1)
7. 7
   Filtrationthe precipitate is filtered
8. 8
   Sonstigedry

Vorschrift

(4-{3-[Benzothiazol-2-yl-(1-methyl-piperidin-4-yloxy)-methyl]-phenylsulfanyl}-butyl)-carbamic acid tert-butyl ester (140 mg) is dissolved in dichloromethane (1 mL) and trifluoroacetic acid (0.4 mL) is added. The reaction mixture is stirred at room temperature for 1 hour. The mixture is evaporated to dryness. The residue is basified by adding a solution of saturated sodium carbonate to pH 10 and the aqueous phase is extracted with dichloromethane. The pooled organic extracts are dried over magnesium sulfate and concentrated under reduced pressure. The residue is purified by chromatography (gradient dichloromethane/methanol/ammonia from 100/0/0 to 90/10/1). The residue is added to oxalic acid (1 equivalent) in acetone (0.5 ml), and the precipitate is filtered and dry to give 4-{3-[benzothiazol-2-yl(1-methylpiperidin-4-yloxy)methyl]phenylsulfanyl}butylamine, oxalate melting at 108° C.

Quelle