1-(chloromethyl)-4-aza-1-azonia bicyclo[2.2.2]octane chloride synthesis
- Product Name:1-(chloromethyl)-4-aza-1-azonia bicyclo[2.2.2]octane chloride
- CAS Number:36273-11-7
- Molecular formula:C7H14Cl2N2
- Molecular Weight:197.1
280-57-9
75-09-2
36273-11-7
General procedure for the synthesis of 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride from triethylenediamine (DABCO) and dichloromethane: 1,4-diazabicyclo[2.2.2]octane (DABCO) (11.2 g, 0.1 mol) was dissolved in 30 mL of dichloromethane, and the reaction mixture was stirred under reflux conditions overnight. Upon completion of the reaction, a white solid was obtained by filtration, washed with dichloromethane (2 x 20 mL) and dried under vacuum to afford 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride in 96% (18.7 g) yield. The product 1-(chloromethyl)-1,4-diazabicyclo[2.2.2]octan-1-ium chloride was characterized as follows: 1H-NMR (500 MHz, D2O) δ 4.97 (s, 2H), 3.40 (t, J = 7.0 Hz, 6H), 3.10 (t, J = 7.5 Hz, 6H); 13C-NMR (125 MHz, D2O) δ 68.2, 51.1, 43.9.
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Yield: 96%
Reaction Conditions:
Reflux;
Steps:
Preparation of 1-(chloromethyl)-4-aza-1-azoniabicyclo[2.2.2]octane chloride
1,4-Diazabicyclo[2.2.2]octane(DABCO) (11.2g, 0.1mol) was added to 30 mL of DCM and the reaction mixture was stirred overnight in reflux condition. The resulting white solid was filtered, washed with DCM (2 × 20mL) and dried under vacuum to give 1-(chloromethyl)-4-aza-1-azoniabicyclo[2.2.2]octanechloride in 96% yield (18.7 g).1-(chloromethyl)-4-aza-1-azoniabicyclo[2.2.2]octanechloride:1H-NMR (500 MHz, D2O)δ 4.97 (s, 2H), 3.40 (t, J = 7.0 Hz, 6H), 3.10 (t, J = 7.5 Hz, 6H); 13C-NMR(125 MHz, D2O) δ 68.2, 51.1, 43.9.
References:
Laali, Kenneth K.;Jamalian, Arezu;Zhao, Chunqing [Tetrahedron Letters,2014,vol. 55,# 49,p. 6643 - 6646] Location in patent:supporting information
280-57-9
576 suppliers
$5.00/5g
75-09-2
1244 suppliers
$10.00/25 mL
36273-11-7
30 suppliers
$262.00/1g
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1000210-73-0
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