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3 reactions in Reaxys
2016-05-20 11h:28m:58s (EST)
F N
1. Query
NH
Search as: As drawn
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F
H N
Cl
F N
N H
N H
Rx-ID: 9177099 View in Reaxys 1/3 Yield
Conditions & References
88 %
5.1.3. General procedure for the synthesis of various substituted benzylpiperazines (3a-s) General procedure: Anhydrous piperazine (6.89 g, 80 mmol) was dissolved in 40 mL of freshly distilled THF. Once the piperazine was fully dissolved, 2.303 mL (20 mmol) of benzyl chloride was added dropwise. The reaction mixture was then refluxed for about 4 h until benzyl chloride disappeared, as assessed by TLC. The stirring mixture was allowed to cool, and then filtered. The filtrate was concentrated in a rotary evaporator and then diluted with EtOAc (100 mL) and water (50 mL), which was then made basic (pH>12) with a saturated 1 N NaOH aqueous solution and separated. The organic phase was washed with water (4 .x. 100 mL), brine (2 .x. 100 mL), dried over Na2SO4 and concentrated to yield an oil. Column chromatography (PE/EtOAc = 1:1 to EtOAc/MeOH = 5:1) afforded a pale yellow liquid. in tetrahydrofuran, Time= 4h, Reflux Zhang, Cunlong; Tan, Chunyan; Zu, Xuyu; Zhai, Xin; Liu, Feng; Chu, Bizhu; Ma, Xiaohua; Chen, Yuzong; Gong, Ping; Jiang, Yuyang; European Journal of Medicinal Chemistry; vol. 46; nb. 4; (2011); p. 1404 - 1414 View in Reaxys
74 %
in toluene, Time= 2h, T= 85 °C Capuano, Ben; Crosby, Ian T.; Lloyd, Edward J.; Taylor, David A.; Australian Journal of Chemistry; vol. 55; nb. 9; (2002); p. 565 - 576 View in Reaxys in acetonitrile, T= 20 °C Ren, Yu; Zhang, Hui Zhen; Zhang, Shao Lin; Luo, Yun Lei; Zhang, Ling; Zhou, Cheng He; Geng, Rong Xia; Journal of Chemical Sciences; vol. 127; nb. 12; (2015); p. 2251 - 2260 View in Reaxys
F
F
N N
O O
N
N H
Rx-ID: 38145135 View in Reaxys 2/3 Yield
Conditions & References 4.1.2 General procedure for the synthesis of 1-(3-substituted benzyl)piperazines 4a–g General procedure: These compounds were prepared by means of the previously reported methods [44]. To a solution of tert-butyl piperazine-1-carboxylate (0.559g, 3.0mmol) and triethylamine (0.63mL, 3.3mmol) in CH2Cl2 (15mL) appropriate substituted benzyl chlorides or benzyl bromides 2a–g (3.6mmol) were added. After stirring the mixture at room temperature overnight, it was then diluted with H2O and the organics extracted with CH2Cl2 (2×20mL), dried over MgSO4, and concentrated under reduced pressure. Purification of the crude material by flash column chromatography (SiO2, PE/AcOEt, 60/40) gave the corresponding intermediates. These intermediates (2.49mmol) were then treated with TFA (5.75mL, 76.8mmol) in toluene (15mL) and stirred for 80min at room temperature. After the removal of the solvent under reduced pressure, the residue was diluted with aqueous NaOH (1N) and the organics extracted with CH2Cl2 (2×20mL), dried over MgSO4, and concentrated under reduced pressure to give the desired compounds 4a–g (72–89percent). With trifluoroacetic acid in toluene, Time= 1.33333h, T= 20 °C
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Sadeghzadeh, Masoud; Sheibani, Shahab; Ghandi, Mehdi; Daha, Fariba Johari; Amanlou, Massoud; Arjmand, Mohammad; Hasani Bozcheloie, Abolfazl; European Journal of Medicinal Chemistry; vol. 64; (2013); p. 488 - 497 View in Reaxys
N NHHCl F
Rx-ID: 28443486 View in Reaxys 3/3 Yield
Conditions & References Oakwood Products, Inc., 1741 Old Dunbar Road, West Columbia, S.C. 29172, USA. TCI America, 9211 N. Harborgate Street, Portland, Oreg. 97203, USA ... 1-(4-ethyl-benzyl)-piperazine hydrochloride; 1 -(2-fluorobenzyl)piperazine; 1-(3-fluorobenzyl)piperazine; 1-(4-fluorobenzyl)piperazine; 1-(3-fluoro-benzyl)-piperazine hydrochloride; 1-(2-fluoro-benzyl)-piper-azine hydrochloride; 1-(2-iodobenzyl)piperazine; 1-(3-iodobenzyl)piperazine; ... Patent; Gillespie, Paul; Goodnow, JR., Robert Alan; Erickson, Shawn David; Jones, Richard; US2009/149466; (2009); (A1) English View in Reaxys
Copyright © 2016 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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