ChemicalBook CAS DataBase List 3-(1-PYRROLIDINO)PROPIONITRILE

3-(1-PYRROLIDINO)PROPIONITRILE synthesis

3synthesis methods

Product Name:3-(1-PYRROLIDINO)PROPIONITRILE
CAS Number:26165-45-7
Molecular formula:C7H12N2
Molecular Weight:124.18

7663-76-5
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26165-45-7
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$16.87/1g

Yield:26165-45-7 44%

Reaction Conditions:

Stage #1:3-(2-oxopyrrolidin-1-yl)propanenitrile with triethyloxonium fluoroborate at 20;Cooling with ice;Inert atmosphere;
Stage #2: with sodium ethanolate in diethyl ether;dichloromethane at -20 - 20;
Stage #3: with platinum on carbon;hydrogen in dichloromethane at 25; under 30003 Torr; for 24 h;

Steps:

35
In a Schlenk vessel cooled in the ice bath, N-(2-cyanoethyl)pyrrolidone-2 (6.9 g, 50 mmol) is admixed with triethyloxonium tetrafluoroborate (10.45 g, 55 mmol) and stirred overnight at room temperature under argon. The ether phase is decanted off and any ether still present is removed in vacuo. The residue is dissolved in dry dichloromethane (40 ml) and added dropwise to a suspension of sodium ethoxide (ethanol-free) in 10 ml of dry diethyl ether at -20° C. Then, the mixture is left overnight to warm to room temperature with vigorous stirring and filtered off from the NaBF₄under argon. The filtrate is concentrated and dissolved in 10 ml of dry dichloromethane. An autoclave is charged with 5% Pt/C (390 mg, 0.2 mol %), flushed with argon and filled with the reaction solution in dichloromethane. 40 bar of hydrogen are then injected in, and the mixture is stirred at 25° C. and constant pressure for 24 hours. After filtering over Celite, the filtrate is dissolved in 40 ml of ice-cold 2N hydrochloric acid and washed with diethyl ether, the aqueous phase is rendered basic under ice cooling with 42 ml of 2N NaOH solution, the product is extracted with diethyl ether (6×20 ml), and the combined organic phases are dried over K₂CO₃. After stripping off the solvent in vacuo, 2.6 g (44%) of virtually clean 3-(1-pyrrolidino)propionitrile are obtained.

References:

Evonik Degussa GmbH;Kadyrov, Renat US2016/272571, 2016, A1 Location in patent:Paragraph 196-197

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123-75-1 Synthesis