Reaction equation
[NH:1]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C([O-])([O-])=O.[Na+].[Na+].I[CH2:22][CH2:23][CH2:24][Si:25]([O:32][CH2:33][CH3:34])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28]>C(#N)C>[CH2:30]([O:29][Si:25]([O:32][CH2:33][CH3:34])([O:26][CH2:27][CH3:28])[CH2:24][CH2:23][CH2:22][N:1]1[CH2:14][CH2:13][CH2:12][NH:11][CH2:10][CH2:9][NH:8][CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1)[CH3:31]Participants
5
Procedure
72 g (0.359 mol) of cyclam and 15 g of Na2CO3 (dried at 100° C. under 1 mm Hg for 24 h) are placed in 2.5 l of acetonitrile in a 6 l reactor under a stream of nitrogen. The mixture is brought to reflux, a solution of 24.2 g (0.073 mol) of iodopropyltriethoxysilane in 500 ml of acetonitrile is then added dropwise and then the reaction mixture is maintained at reflux for 48 h. After evaporating the solvent on a rotary evaporator (still under a nitrogen atmosphere), pentane is added to the residue and the excess cyclam is filtered off. This operation is repeated three times, the filtrates are combined, the pentane is evaporated and compound 1 is obtained in the form of a colorless oil (15 g, 50.8%).
Workup
- temperatureto reflux
- temperaturethe reaction mixture is maintained
- temperatureat reflux for 48 h
- customAfter evaporating the solvent
- customon a rotary evaporator (still under a nitrogen atmosphere), pentane
- additionis added to the residue
- filtrationthe excess cyclam is filtered off
- customthe pentane is evaporated
Sources & evidence
- ORD record
- ord-0514501f0ef044f991efe7780a814ce4
- Source dataset
- uspto-grants-2002_04
- Patent number
- US06372903B1
Linked notes
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