Hydrochloric Acid → 1,4,7,10-Tetraazacyclododecane

HRID 1419460Notes

Reaction equation

HRID 1419460 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][CH2:5][CH2:6][NH2:7].Cl.[OH-].[Na+]>O>[NH:4]1[CH2:5][CH2:6][NH:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2][NH:1][CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8111DiethylenetriamineHCID 14798Sodium Hydroxide

Product 1

HCID 649631,4,7,10-TetraazacyclododecaneYield 28.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

50 g of (II) (0.257 mol) are dissolved in 350 ml of water. 132.5 g of diethylenetriamine (1.285 mol) are added and pH adjusted to 8 with conc. HCl (265 g). The resulting solution is refluxed for 24 h, then cooled, alkalinized with NaOH in pellets, concentrated under vacuum to a residual weight of 350 g and extracted (I) with toluene. The combined organic extracts are concentrated to an about 90 mL volume and left to crystallize. 31.5 g of high quality 1,4,7,10-tetraazacyclododecane are obtained (GC titre: 99.5%). Yield. 71%.

Workup

  1. temperatureThe resulting solution is refluxed for 24 h
  2. temperaturecooled
  3. concentrationconcentrated under vacuum to a residual weight of 350 g
  4. extractionextracted (I) with toluene
  5. concentrationThe combined organic extracts are concentrated to an about 90 mL volume
  6. waitleft
  7. customto crystallize

Sources & evidence

ORD record
ord-4363a140bafc4e42896f4cd4eb25fbb5
Source dataset
uspto-grants-1999_03
Patent number
US05886174

Reaction notes

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