DI-N-PROPYLAMINOACETONITRILE synthesis

5synthesis methods

Product Name:DI-N-PROPYLAMINOACETONITRILE
CAS Number:18071-35-7
Molecular formula:C8H16N2
Molecular Weight:140.23

142-84-7
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$10.00/5mL

107-14-2 Synthesis

107-14-2
275 suppliers
$15.00/25g

18071-35-7
19 suppliers
$28.60/250mg

Yield:18071-35-7 88%

Reaction Conditions:

Stage #1: chloroacetonitrilewith potassium carbonate;potassium iodide in acetonitrile;Reflux;
Stage #2: di-n-propylamine in acetonitrile at 80 - 85; for 20 h;

Steps:

2-(Dipropylamino)acetonitrile (4) [1]

General procedure: To a solution of dipropylamine (23.8 mmol, 4.52 mL) in acetonitrile (140 mL) was added 1.66 g of potassium iodide (0.42 eq, 10.0 mmol) and 13.8 g of potassium carbonate(4 eq, 100.0 mmol). The reaction mixture was refluxed and then was added dropwise a solution of chloroacetonitrile (6.32 mL) in acetonitrile (60 mL). After 20 h at reflux, the mixture was cooled to room temperature, filtrated and evaporated under vacuum. The mixture was diluted in an 1N aqueous hydrochloride acid solution (200 mL) and washed with diethyl ether (3 x 100 mL). The water layer was basified to pH 9 with an 1N aqueous sodium hydroxide solution and extracted with diethyl ether (3 x 100 mL). The organic layer obtained was dried with magnesium sulfate and evaporated under vacuum to give compound 4 as a brown oil (4.06 g, 28.9 mmol, 88%). R_f: 0.70 (Silica gel, eluent mixture A), 0.36 (Silica gel, eluent mixture B); ¹H NMR (CDCl_3,200 MHz) d 0.81 (t, 6H, J = 7.5 Hz, H5), 1.36 (sex, 4H, J = 7.5 Hz, H4), 2.34 (t, 4H, J = 7.5 Hz, H3), 3.45 (s, 2H, H2); ¹³C NMR (CDCl_3,50.3 MHz) d 11.4 (2C5), 20.4 (2C4), 41.5 (C2), 55.8 (2C3), 114.9 (C1).

References:

Vivier, Magali;Rapp, Maryse;Galmier, Marie-Josephe;Jarrousse, Anne-Sophie;Miot-Noirault, Elisabeth;Leal, Fernand;Weber, Valérie;Métin, Jacques;Sauzire, Jacques;Chezal, Jean-Michel;Madelmont, Jean-Claude [European Journal of Medicinal Chemistry,2011,vol. 46,# 11,p. 5705 - 5710] Location in patent:supporting information; experimental part

50-00-0 Synthesis