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Reductive amination history


reductive amination history

The aqueous layer was extracted with ethyl acetate (2 20 mL the combined organic layers were washed with water (2 20 mL dried over sodium sulfate and evaporated under vacuum.
N (1j) 1H cadeau pour les 18 ans d'une copine NMR (300 MHz, site le cadeau de bebe avis CD3OD).10 (t,.0 Hz,.89 (bt,.3 Hz,.836.79 (m,.676.61 (bd,.196.08 (m,.19 (s, 2H 13C NMR (75.4 MHz, CD3OD) 157.8, 157.2, 149.7, 141.5, 129.5, 129.2, 118.3, 113.9, 113.5.N -Allylbenzylamine (1f) 1H NMR (300 MHz, CDCl3).387.08 (m,.89 (ddt,.2,.4,.1 Hz,.215.10 (m,.74 (s,.21 (d,.1 Hz,.00 (bs, 1H 13C NMR (75.4 MHz, CDCl3) 139.6, 136.2, 128.6, 128.1, 127.2, 116.8.N (1c) 1H NMR (300 MHz, CDCl3).198.16 (m,.967.92 (m,.85 (d,.0 Hz,.607.33 (m,.31 (s,.99 (s,.87 (bs, 1H 13C NMR (75.4 MHz, CDCl3) 140.5, 136.1, 134.1, 132.1, 128.9, 128.6, 128.5, 128.0, 127.2.N (1d) 1H NMR (300 MHz, CDCl3).917.88 (m,.577.49 (m,.447.38 (m,.367.30 (m,.01 (s,.89 (s,.16 (bs, 1H 13C NMR (75.4 MHz, CDCl3) 140.4, 137.9, 133.6, 132.9, 128.7, 128.4, 128.3, 127.9, 127.8, 127.2, 126.8, 126.7.Typical experimental procedure, in a round-bottomed flask the aldehyde (5 mmol) and the amine (5 mmol) were suspended in 25 mL of.N (1l) 1H NMR (300 MHz, CD3OD).14 (d,.6 Hz,.90 (td,.6,.9 Hz,.74 (d,.6 Hz,.196.09 (m,.09 (s, 2H 13C NMR (75.4 MHz, CD3OD) 157.7, 155.9, 150.3, 130.9, 129.6, 128.6, 114.9, 105.5.The mixture was vigorously stirred at rt for.N -Hexylbenzylamine (1g) 1H NMR (300 MHz, CDCl3).367.15 (m,.79 (s,.63 (t,.2 Hz,.85 (bs,.50 (quint,.8 Hz,.371.18 (m,.89 (t,.1 Hz, 3H 13C NMR (75.4 MHz, CDCl3) 140.5, 128.5.Characterization data, dibenzylamine (1a) 1H NMR (300 MHz, CDCl3).407.30 (m, 10H.86 (s,.90 (bs, 1H 13C NMR (75.4 MHz, CDCl3) 140.5, 128.6, 128.4, 127.2,.3; esims m / z : calcd for C14H15N, 197.1; found, 198.2 (M H).N (1i) 1H NMR (300 MHz, CD3OD).15 (d,.3 Hz,.87 (t,.8 Hz,.72 (d,.6 Hz,.206.03 (m,.13 (s, 2H 13C NMR (75.4 MHz, CD3OD) 159.0, 157.3, 151.6, 132.1, 130.6, 129.7, 116.1, 106.5, 105.2.N -Benzyl(furan-2-ylmethyl)amine (1b) 1H NMR (300 MHz, CDCl3).407.24 (m,.34 (dd,.1,.8 Hz,.21 (dd,.4,.6 Hz,.80 (bs,.13 (bs, 1H 13C NMR (75.4 MHz, CDCl3) 153.8, 142.0, 139.9, 128.6, 128.4, 127.2, 110.3, 107.2,.9.The reactions were carried out with equimolar amounts of amine and aldehyde using silica gel-sodium borohydride in THF at room temperature.The filtrate and wash solutions were pooled and the organic layer was separated.N -Butylbenzylamine (1e) 1H NMR (300 MHz, CDCl3).377.20 (m,.78 (s,.63 (t,.2 Hz,.98 (bs,.561.45 (m,.411.28 (m,.92 (t,.2 Hz, 3H 13C NMR (75.4 MHz, CDCl3) 140.4, 128.5, 128.3, 127.0,.1.Keywords, aldehydes, Reductive amination, Sodium borohydride, Silica gel.The crude secondary amine was purified by column chromatography using petroleum ether/ethyl acetate.Ethyl acetate (20 mL) was added and the residual zinc powder was filtered and washed with ethyl acetate.N (1k) 1H NMR (300 MHz, CD3OD).16 (d,.6 Hz,.72 (d,.6 Hz,.636.52 (m,.08 (s, 2H 13C NMR (75.4 MHz, CD3OD) 156.9, 150.1, 142.6, 131.5, 129.6, 116.24, 116.21, 115.6,.8; esims m / z : calcd.N -Butylhexylamine (1h) 1H NMR (300 MHz, CDCl3).48 (t,.5 Hz,.46 (b quint,.371.18 (m,.91 (t,.4 Hz,.88 (t,.6 Hz, 3H 13C NMR (75.4 MHz, CDCl3).6,.3,.4,.4,.7,.3,.6.Solution of potassium hydroxide (5 w/v and zinc dust ( 10 m, 98 Sigma-Aldrich) (15 equiv) was added.
Abstract, a simple and convenient procedure for reductive amination of aldehydes using sodium borohydride in the presence of silica gel as an active and inexpensive catalyst is described.



It is considered the most important way to make amines, and.

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