Quinuclidine → n-DODECANOYLOXYMETHYLQUINUCLIDINIUM CHLORIDE

HRID 4720

Reaction equation

HRID 4720 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 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.

Workup

  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°

Sources & evidence

ORD record
ord-fa1c20f388e948989dd21b012d79f7a9
Source dataset
uspto-grants-1988_02
Patent number
US04727151

Linked notes

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