Reductive amination of cyclopentanone

Doležal, Petr; Machalický, Oldřich; Pavelek, M.; Kubec, P.; Hradkova, K.; Hrdina, Radim; Šuláková, Romana

doi:10.1016/j.apcata.2005.03.007

Cited by 15 publications

(5 citation statements)

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“…The kinetics of the reductive amination of cyclopentanone with NH 3 and a catalyst loading of 1 g of Raney Ni per 1 kg of cyclopentanone were studied by Dolezǎl and co-workers in 2005 (Scheme 42). 86 The key seems to be the iminocyclopentane formation. A lower concentration of NH 3 at the beginning of the reaction decreases the rate of amine product formation and increases the formation of byproducts.…”

Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

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The reductive amination, the reaction of an aldehyde or a ketone with ammonia or an amine in the presence of a reducing agent and often a catalyst, is an important amine synthesis and has been intensively investigated in academia and industry for a century. Besides aldehydes, ketones, or amines, starting materials have been used that can be converted into an aldehyde or ketone (for instance, carboxylic acids or organic carbonate or nitriles) or into an amine (for instance, a nitro compound) in the presence of the same reducing agent and catalyst. Mechanistically, the reaction starts with a condensation step during which the carbonyl compound reacts with ammonia or an amine, forming the corresponding imine followed by the reduction of the imine to the alkyl amine product. Many of these reduction steps require the presence of a catalyst to activate the reducing agent. The reductive amination is impressive with regard to the product scope since primary, secondary, and tertiary alkyl amines are accessible and hydrogen is the most attractive reducing agent, especially if large-scale product formation is an issue, since hydrogen is inexpensive and abundantly available. Alkyl amines are intensively produced and use fine and bulk chemicals. They are key functional groups in many pharmaceuticals, agro chemicals, or materials. In this review, we summarize the work published on reductive amination employing hydrogen as the reducing agent. No comprehensive review focusing on this subject has been published since 1948, albeit many interesting summaries dealing with one or the other aspect of reductive amination have appeared. Impressive progress in using catalysts based on earth-abundant metals, especially nanostructured heterogeneous catalysts, has been made during the early development of the field and in recent years.

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Section: Reductive Amination Using Heteregeneous Transition Metal Cat...mentioning

confidence: 99%

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

2020

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“…The action of ammonia on the selectivity of AMP amination to MPDA can be understood considering the formation mechanism of secondary amines. When large amount of ammonia are present in reaction system, they inhibit the formation of their precursor secondary imines ( 8 ) ,. Thus, the byproduct ( 6 ) was mainly formed through Path A.…”

Section: Resultsmentioning

confidence: 99%

Reductive Amination of 2-Amino-2-methyl-1-propanol and Ammonia to Produce 2-Methyl-1,2-propanediamine over Raney Nickel Catalyst

Wang¹,

Yu²,

Zhang³

et al. 2017

ChemistrySelect

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The selective synthesis of 2‐methyl‐1,2‐propyldiamine (MPDA) directly from 2‐amino‐2‐methyl‐1‐propanol (AMP) and ammonia via one‐pot reaction is reported for the first time. The effects of catalyst species and reaction variables on the synthetic performance of MPDA were systematically studied. In contrast to other catalysts, a high MPDA selectivity of 88.3% and AMP conversion of 45.6% were obtained over Raney Ni catalyst. The components of the final reaction mixtures were particularly dependent on the initial hydrogen pressure and stirring speed. Furthermore, a possible mechanism of the reaction was proposed on the basis of experimental results, which has great implications in the development of more efficient and higher selectivity catalysts.

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“…It can effectively inhibit the production of secondary and tertiary amines. In the reductive amination reaction, NH 3 inhibited better than H 2 O, and NH 3 dissolved in the solvent gave better performance [39,40]. Therefore, ammonia-methanol solution was used to improve the selectivity and yield of the hydroreductive amination of oximes to amines.…”

Section: Introductionmentioning

confidence: 99%

Production of Heterocyclic Primary Amines from Heterocyclic Aldehydes on Ni‐Mo/ZrO₂

et al. 2022

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Ni-Mo/ZrO 2 catalysts with Ni-Mo loadings of 10 wt % were prepared by a sol-gel method on a ZrO 2 support and subsequently applied in the simple reductive amination of heterocyclic aldehydes. Among the various catalysts prepared, Ni-Mo/ZrO 2 catalysts with Ni:Mo = 2:1 exhibited the highest metal dispersion and the smallest Ni particle size. The results showed that the catalyst has good catalytic performance, in which the yield of furfurylamine can reach 96.6 %. Initially, oximes were synthesized from the corresponding aldehydes and hydroxylamine hydrochloride, and then heterocyclic primary amines were synthesized by simple hydroreductive amination of the oximes with a 12 % methanolic solution of NH 3 in the presence of an Ni-Mo/ZrO 2 catalyst. The methanolic solution of NH 3 was found to be more effective in inhibiting the formation of secondary and tertiary amines.

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Reductive amination of cyclopentanone

Cited by 15 publications

References 3 publications

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Reductive Amination of 2-Amino-2-methyl-1-propanol and Ammonia to Produce 2-Methyl-1,2-propanediamine over Raney Nickel Catalyst

Production of Heterocyclic Primary Amines from Heterocyclic Aldehydes on Ni‐Mo/ZrO₂

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Reductive amination of cyclopentanone

Cited by 15 publications

References 3 publications

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Transition-Metal-Catalyzed Reductive Amination Employing Hydrogen

Reductive Amination of 2-Amino-2-methyl-1-propanol and Ammonia to Produce 2-Methyl-1,2-propanediamine over Raney Nickel Catalyst

Production of Heterocyclic Primary Amines from Heterocyclic Aldehydes on Ni‐Mo/ZrO2

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Production of Heterocyclic Primary Amines from Heterocyclic Aldehydes on Ni‐Mo/ZrO₂