3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine

We reported an efficient one-pot two-step synthesis of 3-(<i>tert</i>-butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>3</b> in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(<i>tert&...

Full description

Bibliographic Details
Main Authors: Diana Becerra, Hugo Rojas, Juan-Carlos Castillo
Format: Article
Language:English
Published: MDPI AG 2021-03-01
Series:Molbank
Subjects:
Online Access:https://www.mdpi.com/1422-8599/2021/1/M1196
_version_ 1797541944152293376
author Diana Becerra
Hugo Rojas
Juan-Carlos Castillo
author_facet Diana Becerra
Hugo Rojas
Juan-Carlos Castillo
author_sort Diana Becerra
collection DOAJ
description We reported an efficient one-pot two-step synthesis of 3-(<i>tert</i>-butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>3</b> in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(<i>tert</i>-butyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>1</b> and <i>p</i>-methoxybenzaldehyde <b>2</b>. The one-pot reductive amination proceeded by the formation in situ of the <i>N</i>-(5-pyrazolyl)imine <b>4</b> as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized <i>N</i>-heterocyclic amine <b>3</b> was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis.
first_indexed 2024-03-10T13:22:46Z
format Article
id doaj.art-eead7fab062c4b3cab7f488fb1900efe
institution Directory Open Access Journal
issn 1422-8599
language English
last_indexed 2024-03-10T13:22:46Z
publishDate 2021-03-01
publisher MDPI AG
record_format Article
series Molbank
spelling doaj.art-eead7fab062c4b3cab7f488fb1900efe2023-11-21T09:56:26ZengMDPI AGMolbank1422-85992021-03-0120211M119610.3390/M11963-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amineDiana Becerra0Hugo Rojas1Juan-Carlos Castillo2Escuela de Ciencias Química, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja 150003, ColombiaEscuela de Ciencias Química, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja 150003, ColombiaEscuela de Ciencias Química, Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia, Avenida Central del Norte 39-115, Tunja 150003, ColombiaWe reported an efficient one-pot two-step synthesis of 3-(<i>tert</i>-butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>3</b> in good yield by a solvent-free condensation/reduction reaction sequence starting from 3-(<i>tert</i>-butyl)-1-methyl-1<i>H</i>-pyrazol-5-amine <b>1</b> and <i>p</i>-methoxybenzaldehyde <b>2</b>. The one-pot reductive amination proceeded by the formation in situ of the <i>N</i>-(5-pyrazolyl)imine <b>4</b> as key synthetic intermediate of other valuable pyrazole derivatives. This methodology is distinguished by its operational easiness, short reaction time, isolation and purification of the aldimine intermediate is not required. The structure of the synthesized <i>N</i>-heterocyclic amine <b>3</b> was fully characterized by FTIR-ATR, 1D and 2D NMR experiments, EIMS, and elemental analysis.https://www.mdpi.com/1422-8599/2021/1/M11965-aminopyrazolesolvent-free condensationreductive amination<i>N</i>-(5-pyrazolyl)imine<i>N</i>-heterocyclic aminesecondary amine
spellingShingle Diana Becerra
Hugo Rojas
Juan-Carlos Castillo
3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
Molbank
5-aminopyrazole
solvent-free condensation
reductive amination
<i>N</i>-(5-pyrazolyl)imine
<i>N</i>-heterocyclic amine
secondary amine
title 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
title_full 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
title_fullStr 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
title_full_unstemmed 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
title_short 3-(<i>tert</i>-Butyl)-<i>N</i>-(4-methoxybenzyl)-1-methyl-1<i>H</i>-pyrazol-5-amine
title_sort 3 i tert i butyl i n i 4 methoxybenzyl 1 methyl 1 i h i pyrazol 5 amine
topic 5-aminopyrazole
solvent-free condensation
reductive amination
<i>N</i>-(5-pyrazolyl)imine
<i>N</i>-heterocyclic amine
secondary amine
url https://www.mdpi.com/1422-8599/2021/1/M1196
work_keys_str_mv AT dianabecerra 3itertibutylini4methoxybenzyl1methyl1ihipyrazol5amine
AT hugorojas 3itertibutylini4methoxybenzyl1methyl1ihipyrazol5amine
AT juancarloscastillo 3itertibutylini4methoxybenzyl1methyl1ihipyrazol5amine