ChemicalBook CAS DataBase List HEXAMETHYLENEIMINOACETONITRILE

HEXAMETHYLENEIMINOACETONITRILE synthesis

4synthesis methods

Product Name:HEXAMETHYLENEIMINOACETONITRILE
CAS Number:54714-50-0
Molecular formula:C8H14N2
Molecular Weight:138.21

111-49-9
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460-19-5 Synthesis

460-19-5
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54714-50-0
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Yield:54714-50-0 92%

Reaction Conditions:

in water at 5 - 70; for 0.5 h;

Steps:

184

1-Azepanylacetonitrile (290). Azepane (289) (4.9 ml_, 43.8 mmol) was added dropwise to a stirred aqueous solution of glycolonitrile (55%, 5.0 g, 48.2 mmol) at 5 ⁰C and the solution was stirred at 70 ⁰C for 30 min. The solution was cooled, diluted with water (20 mL), washed with Et₂O (3 x 50 ml_). The organic fraction was dried and the solvent evaporated to give nitrile 290 (5.58 g, 92%) as a colourless oil: ¹H NMR δ 3.56 (s, 2 H, CH₂CN), 2.71 (br dd, J = 5.8, 5.5 Hz, 4 H, 2 x CH₂N), 1.67-1.73 (m, 4 H, 2 x CH₂), 1.59- 1.64 (m, 4 H, 2 x CH₂).

References:

WO2006/104406,2006,A1 Location in patent:Page/Page column 168

111-49-9
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107-14-2 Synthesis