Quinuclidine → n-DODECANOYLOXYMETHYLQUINUCLIDINIUM CHLORIDE

HRID 4720

Reaktionsgleichung

Reaktionsgleichung von HRID 4720
[C:1]([O:14][CH2:15][Cl:16])(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[N:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18]2.[K+].[Br-]>CCOCC>[Cl-:16].[C:1]([O:14][CH2:15][N+:17]12[CH2:24][CH2:23][CH:20]([CH2:21][CH2:22]1)[CH2:19][CH2:18]2)(=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

Komponenten

5

Edukt 3

HCID 7527QuinuclidineHCID 253877Potassium BromideHCID 543634Chloromethyl dodecanoate

Produkt 1

HCID 14128213n-DODECANOYLOXYMETHYLQUINUCLIDINIUM CHLORIDE

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

2.49 g (0.01 mol) chloromethyl n-dodecanoate and 1.12 g (0.01 mol) quinuclidine were mixed and allowed to react together at room temperature for 48 hrs. Anhydrous ether was added to the mixture and the mixture was triturated in anydrous ether overnite. The solid was isolated by filtration under a nitrogen atmosphere and thoroughly washed with anhydrous ether. After drying in vacuo over calcium sulfate at room temperature, 2.1 g (0.006 mol), 17 was obtained as a white solid, mp 170°-172°; ir (KBr) 2960, 2930, 1765, 1470, 1120, 1090, 860 and 830 cm-1 ; pmr (CDCl3) δ 5.8 (s, 2H), 3.9 (t, 6H), 2.5 (t, 2H), 2.2 (m, 7H), 1.3 (bs, 18H) and 0.9 (t, 3H) ppm.

Aufarbeitung

  1. customto react together at room temperature for 48 hrs
  2. customthe mixture was triturated in anydrous ether overnite
  3. customThe solid was isolated by filtration under a nitrogen atmosphere
  4. washthoroughly washed with anhydrous ether
  5. dry with materialAfter drying in vacuo over calcium sulfate at room temperature
  6. custom2.1 g (0.006 mol), 17 was obtained as a white solid, mp 170°-172°

Quellen und Nachweise

ORD-Eintrag
ord-fa1c20f388e948989dd21b012d79f7a9
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727151

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