Diphenylphosphinic chloride → 4-[2-(4-Geranyloxybenzoylamino)ethyl]pyridine

HRID 342664Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 342664
[CH2:1]([O:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=O)=[CH:14][CH:13]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:10])[CH3:9])\[CH3:4].C1(P(Cl)(C2C=CC=CC=2)=O)C=CC=CC=1.[NH2:36][CH2:37][CH2:38][C:39]1[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:1]([O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([NH:36][CH2:37][CH2:38][C:39]2[CH:44]=[CH:43][N:42]=[CH:41][CH:40]=2)=[O:18])=[CH:19][CH:20]=1)/[CH:2]=[C:3](/[CH2:5][CH2:6][CH:7]=[C:8]([CH3:9])[CH3:10])\[CH3:4]

Komponenten

6

Edukt 3

HCID 73910Diphenylphosphinic chlorideHCID 832754-PyridineethanamineHCID 123615004-Geranyloxybenzoic acid

Produkt 1

HCID 99296694-[2-(4-Geranyloxybenzoylamino)ethyl]pyridineAusbeute 85,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6212ChloroformLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

4-geranyloxybenzoic acid(1.92 g) was dissolved in chloroform(50 ml) and triethylamine(1.96 ml), and then diphenylphosphinic chloride(1.33 ml) was added thereto while being cooled with ice. After being stirred for 30 minutes, the mixture, with 4-(2-aminoethyl)pyridine(0.94 g) added thereto, was stirred for 2 hours at room temperature. The reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively, dried over sodium sulfate anhydride, and then concentrated under a vacuum. The residue was purified by silica gel column chromatography (chloroform:methanol=30:1), thereby yielding 2.26 g of the aimed compound.

Aufarbeitung

  1. temperaturewhile being cooled with ice
  2. stirringwas stirred for 2 hours at room temperature
  3. washThe reaction mixture was washed with saturated sodium hydrogencarbonate aqueous solution and saturated brine successively
  4. dry with materialdried over sodium sulfate anhydride
  5. concentrationconcentrated under a vacuum
  6. customThe residue was purified by silica gel column chromatography (chloroform:methanol=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-019e1103da1b4d84b417c9100ac84268
Quelldatensatz
uspto-grants-1999_01
Patentnummer
US05859032

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