Quinuclidine → n-DODECANOYLOXYMETHYLQUINUCLIDINIUM CHLORIDE

HRID 971474

Reaction equation

HRID 971474 reaction equation
[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]

Participants

5

Reactant 3

HCID 7527QuinuclidineHCID 253877Potassium BromideHCID 543634Chloromethyl dodecanoate

Product 1

HCID 14128213n-DODECANOYLOXYMETHYLQUINUCLIDINIUM CHLORIDE

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

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 anhydrous 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.

Workup

  1. customto react together at room temperature for 48 hrs
  2. customthe mixture was triturated in anhydrous 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°

Sources & evidence

ORD record
ord-856f122a45cb47ceb9e0c06037a5e544
Source dataset
uspto-grants-1979_07
Patent number
US04160099

Linked notes

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