反应详情

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%.

1. temperatureThis mixture was thereafter refluxed vigorously
2. customThen the solvent was removed at reduced pressure
3. dissolutionthe residue was dissolved in 13 ml of water
4. customThe aqueous solution obtained
5. extractionwas then extracted with chloroform (10 times 3 ml)
6. concentrationthe aqueous layer was concentrated at reduced pressure down to 2 ml
7. customThe product as a white solid was precipitated
8. additionby adding the solution of concentrated HCl and ethanol
9. custompurified
10. customby recrystallizing from ethanol/water/HCl