ChemicalBook CAS DataBase List (S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE

(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE synthesis

3synthesis methods

Product Name:(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE
CAS Number:31886-57-4
Molecular formula:C14H19FeN10*
Molecular Weight:257.15

1277-49-2

124-40-3

(+/-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE

31904-34-4

General procedure for the synthesis of N,N-dimethylamino-1-ferrocenylethylamine from 1-(2-hydroxyethyl)ferrocene and dimethylamine: (3) (S)-1-ferrocenylethanol (1.03 kg, 4.47 mol), dichloromethane (3.0 L), and triethylamine (902.9 g, 8.94 mol) prepared above were added to the reaction vessel sequentially. Acetic anhydride (683.4 g, 6.70 mol) was slowly added dropwise at room temperature and the reaction was stirred for 3 hours. Subsequently, 33% aqueous dimethylamine solution (4.31 kg) was slowly added and stirring was continued for 5 hours. Upon completion of the reaction, the layers were left to separate and the organic phase was concentrated to recover the dichloromethane. The residue was purified by reduced pressure distillation and the fraction at 110 °C (0.07 kPa) was collected to give (S)-N,N-dimethyl-1-ferrocenylethylamine (1.02 kg) as a dark red oily liquid in 89% yield, 98% HPLC purity and 96% ee value.

1277-49-2
163 suppliers
$10.00/250mg

124-40-3
542 suppliers
$18.00/100ml

(S)-(-)-N,N-DIMETHYL-1-FERROCENYLETHYLAMINE

31886-57-4
131 suppliers
$10.00/100mg

Yield:31886-57-4 89%

Reaction Conditions:

Stage #1: 1-ferrocenylethanolwith acetic anhydride;triethylamine in dichloromethane at 20; for 3 h;Large scale;
Stage #2: dimethyl amine in dichloromethane;water; for 5 h;Large scale;Temperature;Solvent;

Steps:

5.3

(3) (S)-1-ferrocenylethanol 2 (1.03 kg, 4.47 mol) prepared above, dichloromethane (3.0 L),Triethylamine (902.9 g, 8.94 mol) was placed in the reaction vessel in turn, acetic anhydride (683.4 g, 6.70 mol) was added dropwise at room temperature, and the reaction was stirred for 3 h;Then slowly add 4.31kg of 33% dimethylamine aqueous solution, continue stirring for 5h; static layering, concentration and concentration to recover dichlorohexane.The residue was distilled under reduced pressure to collect a fraction of 110 ° C (0.07 kPa) to obtain (S)-N,N-Dimethyl-1-ferrocenylethylamine 3 (1.02 kg).Dark red oily liquid, yield: 89%; HPLC purity: 98%; ee: 96%.

References:

CN108409802,2018,A Location in patent:Paragraph 0050; 0053

102-54-5 Synthesis