1,4,7,10-Tetraazacyclododecane → HCID 18913797, compound

HRID 266921Notes

Reaction equation

HRID 266921 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.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH2:17]Br>C(Cl)(Cl)Cl>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH2:17][N: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

Participants

4

Reactant 2

HCID 649631,4,7,10-TetraazacyclododecaneHCID 775162-(Bromomethyl)-1-methoxy-4-nitrobenzene

Product 1

HCID 18913797HCID 18913797, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred chloroform solution (20 ml) containing 2.9 g of 1,4,7,10-tetraazacyclododecane (16.8 mmole) was added a chloroform solution (20 ml) containing 2.1 g of 2-methoxy-5-nitrobenzyl bromide (8.5 mmole) in one portion. After stirring at room temperature for three hours the reaction mixture was filtered and the filtrate concentrated (in vacuo) to give a residue which was chromatographed (silica, Solvent System 3). The monoalkylated product was isolated in 79 percent yield (MP=154°-156° C.), and characterized by:

Workup

  1. filtrationwas filtered
  2. concentrationthe filtrate concentrated (in vacuo)
  3. customto give a residue which
  4. customwas chromatographed (silica, Solvent System 3)
  5. customThe monoalkylated product was isolated in 79 percent yield (MP=154°-156° C.)

Sources & evidence

ORD record
ord-f519d2b699f3406eb905f5043536ebb8
Source dataset
uspto-grants-1997_07
Patent number
US05652361

Reaction notes

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