15190-14-4

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-methoxyphenyl)-2-piperidinoacetonitrile is used as an intermediate in the synthesis of pharmaceuticals for its potential analgesic and anti-inflammatory properties. It is involved in the development of new drugs for the treatment of pain and inflammatory conditions.
Used in Agrochemical Industry:
2-(4-methoxyphenyl)-2-piperidinoacetonitrile is used as an intermediate in the synthesis of agrochemicals, contributing to the development of products for agricultural applications.

InChI:InChI=1/C14H18N2O/c1-17-13-7-5-12(6-8-13)14(11-15)16-9-3-2-4-10-16/h5-8,14H,2-4,9-10H2,1H3

Upstream product

• 151-50-8 potassium cyanide 
• 6091-44-7 piperidine hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 4637-29-0 Bis(1-piperidinyl)acetonitril 
• 2591-86-8 N-Formylpiperidine 
• 7677-24-9 trimethylsilyl cyanide 
• 13139-86-1 4-methoxyphenyl magnesium bromide 
• 100-07-2 4-methoxy-benzoyl chloride 
• 100-09-4 4-methoxybenzoic acid 
• 57700-94-4 N-(p-methoxybenzoyl)piperidine 
• 110-89-4 piperidine 
• 143-33-9 sodium cyanide 

Downstream Products

• 102372-25-8 1-[1-(4-methoxy-phenyl)-3-phenyl-propyl]-piperidine 
• 102700-35-6 1-[1-(4-methoxy-phenyl)-4-phenyl-butyl]-piperidine 
• 127529-36-6 4-methoxydiphenidine 
• 112688-05-8 1-[1-(4-methoxy-phenyl)-3-phenyl-butyl]-piperidine 

Relevant academic research and scientific papers

One-Pot Synthesis of α-Amino Nitrile Units through Alkylative Strecker Cyanation from Formamides

In this work, we describe the one-pot synthesis of α-amino nitrile units by the concomitant addition of alkyl (or aryl) Grignard reagents and TMS cyanide through alkylative Strecker cyanation from readily available formamides. The reaction is broad in sco

Straightforward α-Amino Nitrile Synthesis Through Mo(CO)6-Catalyzed Reductive Functionalization of Carboxamides

The selective reduction of amides into an intermediate hemiaminal catalyzed by Mo(CO)6 together with the inexpensive and easy to handle TMDS (1,1,3,3-tetramethyldisiloxane) as reducing agent, followed by subsequent trapping of the hemiaminal with a cyanide source, allows for the straightforward synthesis of α-amino nitriles. The methodology presented here, displays high levels of chemoselectivity allowing for the reduction of amides in the presence of functional groups such as ketones, imines, aldehydes, and acids, which affords a simple route for the synthesis of α-amino nitriles with a broad scope of functionalities in high yields. Furthermore, the applicability of this methodology is demonstrated by scale up experiments and by derivatization of the target compounds into synthetically interesting products. The selective cyanation is successfully applied in late stage functionalizations of amide containing drugs and prolinol derivatives.

Magnetically separable g-C3N4 hybrid nanocomposite: Highly efficient and eco-friendly recyclable catalyst for one-pot synthesis of α-aminonitriles

A magnetically separable graphitic carbon nitride nanocomposite (Fe3O4/g-C3N4) as a catalyst for the three-component condensation reactions of carbonyl compounds, amines and trimethylsilylcyanide was thoroughly investigated. The reaction of these three components was found to be efficient, economical and green and took place in the presence of a catalytic amount of the magnetically separable catalyst to yield the corresponding α-aminonitriles in good to excellent yields. The prepared nanocomposite was characterized using scanning electron microscopy and energy-dispersive X-ray and Fourier transform infrared spectroscopies. The nanocomposite was also found to be reusable could be recovered easily and reused several times without distinct deterioration in its catalytic activity.

Propylphosphonic anhydride (T3P) catalyzed one-pot synthesis of α-aminonitriles

Abstract The Strecker reaction was performed via a one-pot three component condensation of hetero aromatic/aromatic aldehydes, secondary amines and trimetylsilyl cyanide in the presence of propylphosphonic anhydride (T3P) to accomplish the corresponding α-aminonitriles. The main advantages of this method are very short reaction time and excellent yields.

Superparamagnetic iron oxide as an efficient catalyst for the one-pot, solvent-free synthesis of α-aminonitriles

Superparamagnetic Fe3O4 is shown to act as a very efficient catalyst for the one-pot, three-component synthesis of α-aminonitriles from aldehydes, amines, and TMSCN. The catalyst is easily recovered by the use of an external magnet and reused in several reactions without any noticeable loss of activity. The products are obtained rapidly at room temperature in good purity upon separation of the catalyst and evaporation of the volatiles of the reaction mixture.

One-pot, solvent-free synthesis of α-aminonitriles under catalysis by magnesium bromide ethyl etherate

A three-component, efficient, and facile procedure has been developed for the synthesis of α-aminonitriles from aldehydes, amines, and trimethylsilyl cyanide using a catalytic amount of magnesium bromide ethyl etherate in the absence of solvent. Rapid formation of products is observed at room temperature in a one-pot procedure under very mild conditions giving excellent yields of the title compounds.

Steric Inhibition of Synergistic Radical Stabilizing Effects

Equilibrium acidities in Me2SO for 14 α-N-morpholinyl-, 6 α-N-piperidinyl-, and 7 α-cyclohexylarylacetonitriles and the oxidation potentials of their conjugate bases have been determined.The increased pKHA values by about 2 units observed in these systems, relative to the corresponding arylacetonitriles, is ascribed to the presence of increased steric constraints in the anions.Hammett plots revealed larger ρ values than for arylacetonitriles (6-7 versus 5.5), pointing to an increased negative charge density on the benzylic carbon atoms in the anions.A plot of anion oxidation potentials, Eox(A-), versus pKHA for the α-N-morpholinylarylacetonitriles was linear with a slope near unity, showing that remote substituents for the most part have very little effect on radical stabilities.A 5 and 6 kcal/mol lowering of the BDE of the acidic C-H bond caused by replacing the cyclohexyl group in α-cyclohexylphenylacetonitrile by α-N-morpholinyl or N-piperidinyl groups, respectively, is attributed to the strong donor properties of these amino functions.The effects are only about one-third as large, however, as similar effects in R2NCH2COPh, where the steric effect of Ph is absent and a synergistic effect is believed to be operative.

Orthoamides, XXXIII.-Contributions to the Chemistry of Bis(dialkylamino)acetonitriles

Bis(dialkylamino)acetonitriles 2a-d react with acetyl chloride and antimony pentachloride to give N,N,N',N'-tetraalkylformamidinium hexachloroantimonates 5a-d.Reaction of p-nitrophenol with 2a,b affords N,N,N',N'-tetraalkylformamidinium salts 8a,b, while reaction of aromatic aldehydes 11 with compounds 2 gives aryl(dialkylamino)acetonitriles 12.Phenyl isothiocyanate reacts with the nitriles 2a-c to give 1:1 adducts for which the structure of N,N,N',N'-tetraalkylformamidinium cyano-N-(phenyl)thioformamidates 19 is proposed.N,N,N',N'-Tetraalkylformamidinium p-toluenesulfonates 30a,b have been prepared from nitriles 2a,b and methyl p-toluoenesulfonate (28).Alkylation of 2c with 28 at higher temperatures affords 1,1-dimethylpiperidinium p-toluoenesulfonate (34) and a small amount (1-piperidinyl)malonodinitrile (33).The nitrile 2a reacts with CH acidic compounds such as ethyl cyanoacetate, malonodinitrile and benzyl cyanide to form the enamines 38.