Picolyl chloride hydrochloride → HCID 15293951, compound

HRID 2211081Notes

Reaction equation

HRID 2211081 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8]Cl.[NH:10]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.N1C=CC=CC=1CCl>C(Cl)(Cl)Cl>[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:10]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1

Participants

5

Reactant 3

HCID 23392Picolyl chloride hydrochlorideHCID 23393Picolyl chlorideHCID 649631,4,7,10-Tetraazacyclododecane

Product 1

HCID 15293951HCID 15293951, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A 2-picolyl chloride solution in chloroform was prepared by basifying 3 mL of an aqueous solution of 1.03 g (6.3 mmol) of 2-picolyl chloride hydrochloride to pH>14 and extracting into chloroform. To a stirred chloroform solution of 2.03 g (11.8 mmol) of 1,4,7,10-tetraazacyclododecane was added 10 mL of the prepared 2-picolyl chloride solution in chloroform in one portion. After stirring at temperature for 30 min, the reaction mixture was concentrated in vacuo to give a residue which was chromatographed on sffica gel (column, 2.5×20 cm), eluting with CHCl3 :CH3OH: NH4OH (10:4:1), Rf =0.29 on SiO2 plate. After concentration of eluent, the monoalkylated product was isolated a as thick pale yellow liquid, which upon standing solidified to give 1.17 g of an off-white powder (72%, based on 2-picolyl chloride), and further characterized by:

Workup

  1. extractionextracting into chloroform
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. customto give a residue which
  4. customwas chromatographed on sffica gel (column, 2.5×20 cm)
  5. washeluting with CHCl3 :CH3OH: NH4OH (10:4:1), Rf =0.29 on SiO2 plate
  6. customAfter concentration of eluent, the monoalkylated product was isolated a as thick pale yellow liquid, which
  7. customto give 1.17 g of an off-white powder (72%, based on 2-picolyl chloride)

Sources & evidence

ORD record
ord-ac095792aa9c47aa885df7b58a88c185
Source dataset
uspto-grants-1995_10
Patent number
US05462725

Reaction notes

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