Reaktion #594978

Reaktionsgleichung

Cyclam

4-chloromethylbenzoic acid

→

title compound

Ausbeute 66.6%

4-(1,4,8,11-tetraazacyclotetradec-1-ylmethyl)-benzoic acid

Ausbeute 66.6%

Lösungsmittel

ethanol water

LiOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThis mixture was thereafter refluxed vigorously
2. 2
   SonstigeThen the solvent was removed at reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in 13 ml of water
4. 4
   SonstigeThe aqueous solution obtained
5. 5
   Extraktionwas then extracted with chloroform (10 times 3 ml)
6. 6
   Einengenthe aqueous layer was concentrated at reduced pressure down to 2 ml
7. 7
   SonstigeThe product as a white solid was precipitated
8. 8
   workup.ADDITIONby adding the solution of concentrated HCl and ethanol
9. 9
   Sonstigepurified
10. 10
    Sonstigeby recrystallizing from ethanol/water/HCl

Vorschrift

To solution of Cyclam (0.913 g, 4.5 mmol) dissolved in a mixture of ethanol:water (5:1 by vol.) (18 ml) was added a solution of 4-chloromethylbenzoic acid (0.157 g, 0.92 mmol) in aqueous LiOH (53 mg in 4 ml of water). This mixture was thereafter refluxed vigorously with stirring for 5 hours. Then the solvent was removed at reduced pressure, and the residue was dissolved in 13 ml of water. The aqueous solution obtained was then extracted with chloroform (10 times 3 ml) and the aqueous layer was concentrated at reduced pressure down to 2 ml. The product as a white solid was precipitated by adding the solution of concentrated HCl and ethanol and purified by recrystallizing from ethanol/water/HCl to yield 0.205 g of the title compound. According to the LC-MS, the assay of 4-(1,4,8,11-tetraazacyclotetradec-1-ylmethyl)-benzoic acid hydrochloride was >95%.

Quelle