Lactonitrile → 2-(Diisopropylamino)propionitrile

HRID 374667

Reaction equation

S([O-])([O-])(=O)=O.[Mg+2].[CH:7]([NH:10][CH:11]([CH3:13])[CH3:12])([CH3:9])[CH3:8].[C:14](#[N:18])[CH:15]([CH3:17])O>C(OCC)C>[CH:7]([N:10]([CH:11]([CH3:13])[CH3:12])[CH:15]([CH3:17])[C:14]#[N:18])([CH3:9])[CH3:8]

Participants

Conditions

Temperature: 51 °C

Procedure

Anhydrous magnesium sulfate (12.04 g, 0.1 mol) was added to diisopropylamine (12.14 g, 0.12 mol), followed by lactonitrile (7.73 g of 92% aqueous solution, 0.1 mol) added all at once with stirring. The reaction mixture spontaneously warmed up to 51° C. It was left overnight at room temperature. Diethyl ether (50 ml) was added, and magnesium sulfate was filtered off and washed with ether (50 ml). The product was isolated by distillation, 11.57 g, 75% yield, bp 49°-50° C./0.1 mm Hg. 1H NMR CDCl3 δ ppm, 1.02 (d, J=6.5 Hz, 6H, CH3), 1.17 (d, J=6.5 Hz, 6H, CH3), 1.41 (d, J=6.5 Hz, 3H, CH3, 3.21 (sep, J=6.5 Hz, 2H,=CH) , 3.89 (q, J=6.5 Hz, 1H, CH) .

Workup

additionadded all at once
filtrationmagnesium sulfate was filtered off
washwashed with ether (50 ml)
customThe product was isolated by distillation, 11.57 g, 75% yield, bp 49°-50° C./0.1 mm Hg

Sources & evidence

ORD record: ord-c47826333e954a139ba74d6485ed7449
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05481038

Linked notes

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