N-(3-Aminopropyl)morpholine synthesis
- Product Name:N-(3-Aminopropyl)morpholine
- CAS Number:123-00-2
- Molecular formula:C7H16N2O
- Molecular Weight:144.21
4542-47-6
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123-00-2
The general procedure for the synthesis of morpholine and 3-(4-morpholinyl)-1-propanamine from 3-(4-morpholinyl)propanenitrile was as follows: sodium borohydride (0.6 g, 0.016 mol), 15 mL of tert-butanol, anhydrous nickel(II) chloride (1.0 g, 0.008 mol), and 3-(4-morpholinyl)propanenitrile (14 g, 0.1 mol) were added to the reaction system. The reaction was carried out at 70 °C for 8 hours. Upon completion of the reaction, morpholine (product 1) was obtained in 22 wt%. The results of mass spectral analysis were as follows: m/e (relative intensity, %): 88.8 (2) [M + 2], 87.9 (59) [M + 1], 86.8 (67) [M], 86.0 (100), 56.9 (86), 55.9 (98), 41.9 (28). Also, 3-N-morpholino-1-aminopropane (product 2) was obtained at 59 wt%. The results of mass spectrometry analysis were as follows: m/e (relative intensity, %): 145.0 (5) [M + 1], 128.0 (1.5), 126.8 (7), 113.0 (32), 101.0 (11), 100.0 (100), 86.0 (7), 72.0 (10), 70.0 (30), 57.0 (11), 56.0 (35 ), 42.0 (30).
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Yield:123-00-2 86%
Reaction Conditions:
with hydrazine hydrate in ethanol for 24 h;Reflux;
Steps:
4.1.13.1. General procedures for the preparation of compounds 7b-f and 7h-l
General procedure: To a solution of compounds 6b-l (9.15 mmol) in 30 mLEtOH was added hydrazine monohydrate (36.6 mmol; 4 eq.) andthe mixture was vigorously stirred under reflux for 24 h. The whitesolid was filtered off and washed with EtOH. Filtrate was concentratedunder vacuum to dryness and taken up with EtOAc. The solidresidue was filtered again and filtrate was concentrated in vacuo toafford the desired products 7b-7l. NH2 signals are missing for allcompounds in 1H NMR spectra.
References:
Tazarki, Helmi;Zeinyeh, Wael;Esvan, Yannick J.;Knapp, Stefan;Chatterjee, Deep;Schr?der, Martin;Joerger, Andreas C.;Khiari, Jameleddine;Josselin, Béatrice;Baratte, Blandine;Bach, Stéphane;Ruchaud, Sandrine;Anizon, Fabrice;Giraud, Francis;Moreau, Pascale [European Journal of Medicinal Chemistry,2019,vol. 166,p. 304 - 317]
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123-00-2
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![4-Morpholinepropanamine, N-[3-(4-morpholinyl)propyl]-](/CAS/20210111/GIF/18889-29-7.gif)