N,N-dimethyl-p-phenylenediamine → N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamine

HRID 1457599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1457599
[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[CH:11](=O)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.C(=O)([O-])O.[Na+]>ClCCl.C(O)(=O)C>[CH3:1][N:2]([CH3:10])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])=[CH:5][CH:4]=1

Komponenten

7

Edukt 4

HCID 7472N,N-dimethyl-p-phenylenediamineHCID 8130HeptanalHCID 516892Sodium BicarbonateHCID 2724942Triacetoxyborohydride

Produkt 1

HCID 22099398N4-Heptyl-N1,N1-dimethyl-1,4-benzenediamineAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 3.50 g of N,N-dimethyl-p-phenylenediamine, 4.592 g of heptanal, 9.095 g of triacetoxyborohydride, 1.841 g of acetic acid and 257 ml of dichloromethane was stirred at room temperature for one hour. A saturated sodium hydrogen carbonate solution is added to the mixture, and the mixture was extracted with ethyl acetate. The extract was washed and dried, and the solvent was removed under reduced pressure. The residue obtained was purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1) to give 2.819 g of N,N-dimethyl-N'-heptyl-p-phenylenediamine (yield: 39%, oily product, IR (film): 3375, 2927, 1519 cm-1).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed
  3. customdried
  4. customthe solvent was removed under reduced pressure
  5. customThe residue obtained
  6. customwas purified by silica gel column chromatography (solvent; hexane:ethyl acetate=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-a456221f39354a91800f7687886e9831
Quelldatensatz
uspto-grants-1998_12
Patentnummer
US05849732

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