1,4,7,10-Tetraazacyclododecane → HCID 14951032, compound

HRID 1648165Notes

Reaction equation

HRID 1648165 reaction equation
[NH:1]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1)([O-:15])=[O:14]>C(Cl)(Cl)Cl>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH2:20][N:1]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 649631,4,7,10-TetraazacyclododecaneHCID 660114-Nitrobenzyl bromide

Product 1

HCID 14951032HCID 14951032, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
25 °C

Procedure

In 50 ml of chloroform was added 3.5 g (20.3 mmole) of 1,4,7,10-tetraazacyclododecane and 1.7 g (7.87 mmole) p-nitrobenzyl bromide and the mixture stirred under nitrogen for 24 hours at 25° C. The chloroform slurry of hydrobromide salt was then applied to a 1 in.×17 in. column of flash silica gel (Solvent System 3). There was obtained 2.13 g (6.93 mmole) of the title product as a pale yellow solid of analytical purity in 88 percent yield (Rf =0.58, Solvent System 3), MP=128°-129° C., and further characterized by:

Sources & evidence

ORD record
ord-abb83eb9ea6e44e78f41c7dbddfabb4c
Source dataset
uspto-grants-1995_07
Patent number
US05435990

Reaction notes

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