Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7].[N-:8]=[N+:9]=[N-:10].[Na+]>CN(C)C=O.O>[N:8]([CH2:2][CH2:3][CH2:4][CH2:5][C:6]#[N:7])=[N+:9]=[N-:10]A solution of 5-bromovaleronitrile (48.6 g, 0.3 mol) in N, N-dimethylformamide (600 ml) was treated with sodium azide (23.4 g, 0.36 mol) and stirred at 100° C. for 4 h. The reaction mixture was cooled to 23° C. and diluted with water (500 ml); the resulting solution was extracted with ether (4×400 ml). The ether extracts were combined, washed with water (3×200 ml) and dried over anhydrous magnesium sulfate. The evaporation of ether under reduced pressure gave a yellow liquid which was distilled under high vacuum; bp 83°-4° C. (0.6 mm)1 ; 1Hmr (CDCl3) δ: 3.37 (2H, m, δ-H), 2.4 (2H, m, α-H) and 2.0-1.3 ppm (4H, β-H and γ-H).
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