Triethylamine → HCID 54346618, compound

HRID 1292554Notes

Reaction equation

HRID 1292554 reaction equation
Cl.Cl.[CH3:3][N:4]([CH2:6][CH2:7][CH2:8][NH:9][CH2:10][CH:11]([OH:20])[CH2:12][NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[CH3:5].C(N([CH2:26][CH3:27])CC)C.[C:28](Cl)(=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].[OH-:36].[Na+]>C(O)C.C(Cl)Cl>[O:34]=[C:28]([N:13]([CH2:12][CH:11]([OH:20])[CH2:10][N:9]([C:28](=[O:36])[CH2:29][CH2:30][CH2:31][CH2:26][CH3:27])[CH2:8][CH2:7][CH2:6][N:4]([CH3:5])[CH3:3])[CH2:14][CH2:15][CH2:16][N:17]([CH3:18])[CH3:19])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 67340Hexanoyl chlorideHCID 88307450HCID 88307450, compound

Product 1

HCID 54346618HCID 54346618, compoundYield 48.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6344DichloromethaneSolvent

Procedure

2,14-Dimethyl-8-hydroxy-2,6,10,14-tetrazapentadecane 2HCl (30 g, 0.09 mol) synthesized in accordance with the method described in DE2616411, triethylamine (62 ml, 0.45 mol), and methylene chloride (600 ml) were placed in a 1-liter four-necked round flask, and the mixture was cooled on ice. Hexanoylchloride (36.3 g, 0.27 mol) was added dropwise over 3 hours to the flask while the contents of the flask were stirred under nitrogen. The mixture was stirred for 24 more hours at room temperature. The solid which precipitated was removed by filtration, and the solvent was removed under reduced pressure. Ethanol (600 ml) and an aqueous 4N NaOH solution (225 ml, 0.9 mol) were added to the residue and the mixture was stirred at 40° C. for 3 hours. The solvent was removed under reduced pressure. Methylene chloride was added and extraction was performed. After methylene chloride was removed from the organic phase under reduced pressure, the residue was purified by column chromatography (packed with Kieselgel 60 (product of Merck), eluent:chloroform/methanol=7:1 (v/v)) to obtain 20 g of 4,8-bis(1-oxohexyl)-1,11-di(dimethylamino)-6-hydroxy-4,8-diazaundecane. Yield: 50 wt %.

Workup

  1. customwere placed in a 1-liter four-necked round flask
  2. temperaturethe mixture was cooled on ice
  3. stirringThe mixture was stirred for 24 more hours at room temperature
  4. customThe solid which precipitated
  5. customwas removed by filtration
  6. customthe solvent was removed under reduced pressure
  7. stirringthe mixture was stirred at 40° C. for 3 hours
  8. customThe solvent was removed under reduced pressure
  9. additionMethylene chloride was added
  10. extractionextraction
  11. customAfter methylene chloride was removed from the organic phase under reduced pressure
  12. customthe residue was purified by column chromatography (packed with Kieselgel 60 (product of Merck), eluent:chloroform/methanol=7:1 (v/v))

Sources & evidence

ORD record
ord-c6d28468fab94e878951affbaea4a832
Source dataset
uspto-grants-1998_05
Patent number
US05756784

Reaction notes

Loading…