Palmitoyl chloride → 1,2-Dipalmitoyl-3-dimethylammonium-propane

HRID 217090

Reaktionsgleichung

Reaktionsgleichung von HRID 217090
[CH3:1][N:2]([CH3:8])[CH2:3][CH:4]([OH:7])[CH2:5][OH:6].C(N([CH2:14][CH3:15])CC)C.[C:16](Cl)(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][N:2]([CH2:3][CH:4]([O:7][C:16](=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:14][CH3:15])[CH2:5][O:6][C:16](=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH3:8]

Komponenten

6

Edukt 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 790783-(Dimethylamino)-1,2-propanediol

Produkt 1

HCID 105315561,2-Dipalmitoyl-3-dimethylammonium-propane

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

43.17 g 3-(dimethylamino)-1,2-propanediol were dissolved on 1000 ml dichloromethane. After the addition of 73.3 g triethylamine and 0.01 g 4-dimethylamino pyridine the mixture was cooled down to 0° C. Then 199.18 g hexadecanoic acid chloride, dissolved in 100 ml dichloromethane, were added dropwise. After the addition of another 100 ml dichloromethane the mixture was brought to room temperature and allowed to stir over night. The mixture was filtered and the residue washed with 300 ml dichloromethane. The solvent of the filtrate was removed using a rotary evaporator and the crude product was purified by column chromatography on silica gel (eluent: acetic acid ethyl ester/petrolether 1:1). The product was characterized by 1H-NMR.

Aufarbeitung

  1. additionwere added dropwise
  2. customwas brought to room temperature
  3. filtrationThe mixture was filtered
  4. washthe residue washed with 300 ml dichloromethane
  5. customThe solvent of the filtrate was removed
  6. customa rotary evaporator
  7. customthe crude product was purified by column chromatography on silica gel (eluent: acetic acid ethyl ester/petrolether 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-c9d201d239ea43d687bb637ec02ba106
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193246B2

Verknüpfte Notizen

Wird geladen…