4-Isobutenylmorpholine synthesis
- Product Name:4-Isobutenylmorpholine
- CAS Number:2403-55-6
- Molecular formula:C8H15NO
- Molecular Weight:141.21
110-91-8
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78-82-0
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10315-98-7
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2403-55-6
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Yield:10315-98-7 42 %Spectr. ，2403-55-6 46 %Spectr.
Reaction Conditions:
with nickel;hydrogen at 70; under 760.051 Torr; for 16 h;
Steps:
Hydrogenation of butyronitrile 1a in the presence of piperidine 6a.
General procedure: To a suspension of 0.4 g (0.012 mol) of sodium borohydride in 20 mL of piperidine 6a at 30°C was added 0.8 g (0.006 mol) of anhydrous nickel(II) chloride. The mixture was heated to 60°C to produce black colloid solution of a catalyst. Butyronitrile (6.9 g, 0.1 mol) was added to the resulting catalyst, and hydrogen was passed at 70°C for 14 h. After cooling, 1 mL of water was added to the mixture to accelerate the catalyst coagulation. The precipitate was filtered off, the filtrate was analyzed. N-n-Butylidene-n-butylamine (5a), content 8%. Mass spectrum, m/e (Irel, %): 128.8 (13) [M + 2], 127.8 (100) [M + 1], 125.9 (4), 111.9 (16), 85.1 (8), 84.1 (53), 83.2 (9), 70.2 (16), 57.2 (26), 56.2 (30), 55.2 (10), 42.1 (50), 41.2 (34), 40.2 (3). N-n-Butylpiperidin (7a), content 19%. Mass spectrum, m/e (Irel,%): 141.9 (6) [M + 1], 140.7 (2) [M], 139.9 (5), 98.9 (6), 98.0 (100), 70.0 (10), 42.1 (7). N-1-Butyl-1-idenpiperidin (8a), content 39%. Mass spectrum, m/e (Irel, %): 139.9 (4) [M + 1], 138.8 (20) [M], 138.0 (7), 125.0 (9), 124.0 (100), 110.0 (8), 96.0 (4), 94.0 (5), 68.0 (20), 42.2 (6), 41.2 (9). N-1-Butyl-1-idendi-nbutylamine (9), content 31%. Mass spectrum, m/e (Irel, %): 183.0 (12) [M], 182.0 (100), 181.1 (9), 152.2 (6), 124.0 (5), 41.2 (3).
References:
Popov, Yu. V.;Mokhov;Shcherbakova [Russian Journal of General Chemistry,2016,vol. 86,# 4,p. 798 - 805][Zh. Obshch. Khim.,2016,vol. 86,# 4,p. 609 - 616,8]
4394-85-8
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2403-55-6
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