Potassium Carbonate → 1-(4-Vinylbenzyl)-1,4,8,11-tetraazacyclotetradecane

HRID 78386

Reaction equation

HRID 78386 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:15](=O)([O-])[O-].[K+].[K+].ClC[CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CN(C=O)C>[CH:24]([C:25]1[CH:26]=[CH:27][C:28]([CH2:15][N:1]2[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]2)=[CH:29][CH:30]=1)=[CH2:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 649641,4,8,11-TetraazacyclotetradecaneHCID 94242Benzene, (3-chloro-1-propenyl)-

Product 1

HCID 151342551-(4-Vinylbenzyl)-1,4,8,11-tetraazacyclotetradecaneYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

40 g of cyclam (1) (200 mmol) are dissolved in 1 L of DMF at 70° C. 25 g (181 mmol) of potassium carbonate are added to the solution. A solution of 5.9 g (38.7 mmol) of chloromethylstyrene in 500 ml of DMF is added by slow dropwise addition (9 hours) with stirring. The reaction medium is stirred at 70° C. for an additional hour. After returning to ambient temperature, the excess cyclam and potassium carbonate is removed by filtration. The filtrate is evaporated and the residue is then taken up in diethyl ether. After evaporating the solvent, the compound is obtained in the form of a light yellow oil (11.2 g; 35.4 mmol). Yield: 91%.

Workup

  1. stirringThe reaction medium is stirred at 70° C. for an additional hour
  2. customAfter returning to ambient temperature
  3. customthe excess cyclam and potassium carbonate is removed by filtration
  4. customThe filtrate is evaporated
  5. customAfter evaporating the solvent
  6. customthe compound is obtained in the form of a light yellow oil (11.2 g; 35.4 mmol)

Sources & evidence

ORD record
ord-2091d3679d8f4e3e96e8b80778d56780
Source dataset
uspto-grants-2014_09
Patent number
US08841384B2

Linked notes

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