An efficient and practical method for highly chemoselective hydrogenation of nitrobenzylamines to aminobenzylamine hydrochlorides

被引：5

作者：

Cheng, Chuanjie ^{[1
]}

Wang, Xinyan ^{[1
]}

Xing, Lixin ^{[1
]}

Liu, Bo ^{[1
]}

Zhu, Rui ^{[1
]}

Hu, Yuefei ^{[1
]}

机构：

[1] Tsinghua Univ, Dept Chem, Minist Educ, Key Lab Bioorgan Phosphorous Chem & Chem Biol, Beijing 100084, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2007年 / 349卷 / 10期

关键词：

amines; chemoselectivity; hydrogenation; palladium; reduction;

D O I：

10.1002/adsc.200600521

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Aqueous hydrochloric acid proved to be a very reliable modulator for adjusting the reactivity of palladium on carbon. Thus an efficient and practical method for the highly chemoselective hydrogenation of N,N-dialkylnitrobenzylamines to amino-N,N-dialkylbenzylamine hydrochlorides was established.The method features convenient performance, easy work-up and high efficiency.

引用

收藏

页码：1775 / 1780

页数：6

相关论文

共 36 条

[1] Dimeric self-assembling capsules derived from the highly flexible tribenzylamine skeleton [J].

Alajarín, M ;

Pastor, A ;

Orenes, RA ;

Steed, JW .

JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (20) :7091-7095

[2] Synthesis of 1-benzothiepine and 1-benzazepine derivatives as orally active CCR5 antagonists [J].

Aramaki, Y ;

Seto, M ;

Okawa, T ;

Oda, T ;

Kanzaki, N ;

Shiraishi, M .

CHEMICAL & PHARMACEUTICAL BULLETIN, 2004, 52 (02) :254-258

[3] N-[4-(1,1′-biphenyl)methyl]-4-(4-thiomorpholinylmethyl)benzenamines as non-oxazolidinone analogues of antimycobacterial U-100480. [J].

Artico, M ;

Mai, A ;

Sbardella, G ;

Massa, S ;

Lampis, G ;

Deidda, D ;

Pompei, R .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1998, 8 (12) :1493-1498

[4] New series of morpholine and 1,4-oxazepane derivatives as dopamine D4 receptor ligands:: Synthesis and 3D-QSAR model [J].

Audouze, K ;

Nielsen, EO ;

Peters, D .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (12) :3089-3104

[5] A small-molecule, nonpeptide CCR5 antagonist with highly potent and selective anti-HIV-1 activity [J].

Baba, M ;

Nishimura, O ;

Kanzaki, N ;

Okamoto, M ;

Sawada, H ;

Iizawa, Y ;

Shiraishi, M ;

Aramaki, Y ;

Okonogi, K ;

Ogawa, Y ;

Meguro, K ;

Fujino, M .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1999, 96 (10) :5698-5703

[6] Novel azido and isothiocyanato analogues of [3-(4-phenylalkylpiperazin-1-yl)propyl]bis(4-fluorophenyl)amines as potential irreversible ligands for the dopamine transporter [J].

Cao, JJ ;

Lever, JR ;

Kopajtic, T ;

Katz, JL ;

Pham, AT ;

Holmes, ML ;

Justice, JB ;

Newman, AH .

JOURNAL OF MEDICINAL CHEMISTRY, 2004, 47 (25) :6128-6136

[7] Discovery and structure-activity relationship of N-(ureidoalkyl)-benzyl-piperidines as potent small molecule CC chemokine receptor-3 (CCR3) antagonists [J].

De Lucca, GV ;

Kim, UT ;

Johnson, C ;

Vargo, BJ ;

Welch, PK ;

Covington, M ;

Davies, P ;

Solomon, KA ;

Newton, RC ;

Trainor, GL ;

Decicco, CP ;

Ko, SK .

JOURNAL OF MEDICINAL CHEMISTRY, 2002, 45 (17) :3794-3804

[8] Development of an efficient synthesis of the pyrrolquinolone PHA-529311 [J].

Dorow, RL ;

Herrinton, PM ;

Hohler, RA ;

Maloney, MT ;

Mauragis, MA ;

McGhee, WE ;

Moeslein, JA ;

Strohbach, JW ;

Veley, MF .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2006, 10 (03) :493-499

[9] THE DISCOVERY OF POTENT NONPEPTIDE ANGIOTENSIN-II RECEPTOR ANTAGONISTS - A NEW CLASS OF POTENT ANTIHYPERTENSIVES [J].

DUNCIA, JV ;

CHIU, AT ;

CARINI, DJ ;

GREGORY, GB ;

JOHNSON, AL ;

PRICE, WA ;

WELLS, GJ ;

WONG, PC ;

CALABRESE, JC ;

TIMMERMANS, PBMWM .

JOURNAL OF MEDICINAL CHEMISTRY, 1990, 33 (05) :1312-1329

[10] Highly selective, novel analogs of 4-[2-(diphenylmethoxy)ethyl]-1-benzylpiperidine for the dopamine transporter: Effect of different aromatic substitutions on their affinity and selectivity [J].

Dutta, AK ;

Coffey, LL ;

Reith, MEA .

JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (01) :35-43

← 1 2 3 4 →