Reaction #4816

Reaction equation

chloromethyl n-dodecanoate

quinuclidine

KBr

→

n-Dodecanoyloxymethylquinuclidinium Chloride

Solvents

ether

Conditions

Workup

1. 1
   Otherto react together at room temperature for 48 hrs
2. 2
   Otherthe mixture was triturated in anydrous ether overnite
3. 3
   OtherThe solid was isolated by filtration under a nitrogen atmosphere
4. 4
   Washthoroughly washed with anhydrous ether
5. 5
   DryingAfter drying in vacuo over calcium sulfate at room temperature
6. 6
   Other2.1 g (0.006 mol), 17 was obtained as a white solid, mp 170°-172°

Procedure

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.

Source