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5 reactions in Reaxys
2018-06-06 17h:34m:17s (UTC)
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Search as: Product, As drawn, No mixtures ))
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Rx-ID: 42226859 View in Reaxys 1/5 Yield
Conditions & References Reaction Steps: 3 1: triethylamine / isopropyl alcohol / 1 h / 20 - 35 °C 2: hydrogenchloride / isopropyl alcohol / 9 h / 50 °C 3: triethylamine / acetonitrile / 3.5 h / 50 °C With hydrogenchloride, triethylamine in isopropyl alcohol, acetonitrile Patent; NEURALSTEM, INC.; Venkatraman, Sripathy; Mahmood, Syed; Mobele, Bingidimi I.; Lapina, Olga; Vercoe, Kellie; Li, Ying; Salsbury, Jonathan; McLaws, Mark; (14 pag.); US9278933; (2016); (B2) English View in Reaxys
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Rx-ID: 42226864 View in Reaxys 2/5 Yield
Conditions & References Reaction Steps: 2 1: hydrogenchloride / isopropyl alcohol / 9 h / 50 °C 2: triethylamine / acetonitrile / 3.5 h / 50 °C With hydrogenchloride, triethylamine in isopropyl alcohol, acetonitrile Patent; NEURALSTEM, INC.; Venkatraman, Sripathy; Mahmood, Syed; Mobele, Bingidimi I.; Lapina, Olga; Vercoe, Kellie; Li, Ying; Salsbury, Jonathan; McLaws, Mark; (14 pag.); US9278933; (2016); (B2) English View in Reaxys H N
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HCl O
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Rx-ID: 42226868 View in Reaxys 3/5 Yield
Conditions & References 4.D : Conversion to 1E (Steps 3 and 4) D. Alternatively, to an 8.0 g sample of 3E.HCl in acetonitrile (48 mL, 6 vol) was added triethylamine (2.5 equiv) followed by benzyl chloride (1.05 equiv). The resulting suspension was heated to 50° C. when it turned into a clear solution. The reaction was monitored by HPLC and was judged complete after 3.5 hours (3.3percent of unreacted 3E.HCl). The reaction mixture was cooled to ambient temperature and the solids (TEA.HCl salt) were filtered. (0096) The filtrate was evaporated to adjust the weight of the solution to 18 g (≈1:1 acetonitrile/product by weight). To this was added isoamylamine (≈4:1 isoamylamine/acetonitrile, 10 equiv of isoamylamine) and the resulting solution was heated to 85° C. The reaction was judged complete by HPLC analysis after 19 hours (3.0percent of unreacted 2E). The reaction mixture was cooled to ambient temperature and the solvent was removed under reduced pressure to adjust weight of the solution to 22 g (1 g of solvent per gram of 1E). On cooling a wet
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solid was obtained and this was triturated with heptanes (6 g per gram of 1E). The suspension was stirred at ambient temperature for 16 hours and the solids were collected by filtration on a Whatman® 1 filter paper and the filter cake was washed with heptanes (20 mL), followed by water (2×20 mL). The product was dried in a vacuum oven at ambient temperature to afford 7.78 g (69percent yield over two steps) of 1E as a light brown solid. HPLC purity was >99.9percent (AUC 226 nm). With triethylamine in acetonitrile, Time= 3.5h, T= 50 °C , Time Patent; NEURALSTEM, INC.; Venkatraman, Sripathy; Mahmood, Syed; Mobele, Bingidimi I.; Lapina, Olga; Vercoe, Kellie; Li, Ying; Salsbury, Jonathan; McLaws, Mark; (14 pag.); US9278933; (2016); (B2) English View in Reaxys
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Rx-ID: 42226874 View in Reaxys 4/5 Yield
Conditions & References Reaction Steps: 4 1: thionyl chloride; N,N-dimethyl-formamide / 3.08 h / 65 °C 2: triethylamine / isopropyl alcohol / 1 h / 20 - 35 °C 3: hydrogenchloride / isopropyl alcohol / 9 h / 50 °C 4: triethylamine / acetonitrile / 3.5 h / 50 °C With hydrogenchloride, thionyl chloride, triethylamine, N,N-dimethyl-formamide in isopropyl alcohol, acetonitrile Patent; NEURALSTEM, INC.; Venkatraman, Sripathy; Mahmood, Syed; Mobele, Bingidimi I.; Lapina, Olga; Vercoe, Kellie; Li, Ying; Salsbury, Jonathan; McLaws, Mark; (14 pag.); US9278933; (2016); (B2) English View in Reaxys O
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Rx-ID: 25562737 View in Reaxys 5/5 Yield
Conditions & References Patent; Lorsbach, Beth Anne; Ruiz, James Melvin; Sparks, Thomas Clarence; Sullenberger, Michael Thomas; Morrison, Irene Mae; Webster, Jeffery Dale; US2007/4750; (2007); (A1) English View in Reaxys
Copyright © 2018 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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