2516-47-4Relevant academic research and scientific papers
Preparation method of cyclopropyl methylamine
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Paragraph 0012; 0013; 0014; 0015, (2019/08/14)
The invention relates to a preparation method of cyclopropyl methylamine. The preparation method includes the following steps that cyclopropyl cyanide, nickel dichloride and tetrahydrofuran are addedinto a reaction container, stirring is started, sodium borohydride is added in batches under nitrogen protection, the reaction temperature is controlled at 20-45 DEG C, and the reaction time is 10-18hours; the temperature is reduced to room temperature after reacting is completed, water is added into reaction liquid for stirring, the material stands still for layering, liquid is separated, a water layer is extracted with dichloromethane multiple times, organic phases are combined, the organic phases are dried with anhydrous sodium sulfate, and filtering is carried out; the organic phases aretransferred into a rectification bottle, constant-pressure rectification is carried out, and products with the peak temperatures of 83-85 DEG C are collected; obtained disqualified former fractions are rectified again, colorless transparent liquid obtained twice are combined, and the target product cyclopropyl methylamine is obtained. The cyclopropyl cyanide serves as the initial raw material, cyan is reduced with a sodium borohydride/nickel dichloride system, and the cyclopropyl methylamine is synthesized. The raw materials involved in the synthesis method are cheap, the reaction conditions are mild, and the synthesis method is easy to operate, safe, reliable, simple in aftertreatment and suitable for industrial production.
Electron transfer reduction of nitriles using SmI2-Et 3N-H2O: Synthetic utility and mechanism
Szostak, Michal,Sautier, Brice,Spain, Malcolm,Procter, David J.
supporting information, p. 1092 - 1095 (2014/03/21)
The first general reduction of nitriles to primary amines under single electron transfer conditions is demonstrated using SmI2 (Kagan's reagent) activated with Lewis bases. The reaction features excellent functional group tolerance and represents an attractive alternative to the use of pyrophoric alkali metal hydrides. Notably, the electron transfer from Sm(II) to CN functional groups generates imidoyl-type radicals from bench stable nitrile precursors.
C-H functionalization of cyclopropanes: A practical approach employing a picolinamide auxiliary
Roman, Daniela Sustac,Charette, Andre B.
supporting information, p. 4394 - 4397 (2013/09/24)
A Pd-catalyzed, picolinamide-enabled, and efficient C-H arylation of cyclopropanes is described. The reaction can be promoted by either a silver additive or catalytic pivalic acid in the presence of a carbonate base. Various aryl iodides can be employed as coupling partners, providing exclusively cis-substituted cyclopropylpicolinamides.
A convenient approach to synthesizing peptide C-terminal N-alkyl amides
Fang, Wei-Jie,Yakovleva, Tatyana,Aldrich, Jane V.
, p. 715 - 722 (2013/05/09)
Peptide C-terminal N-alkyl amides have gained more attention over the past decade due to their biological properties, including improved pharmacokinetic and pharmacodynamic profiles. However, the synthesis of this type of peptide on solid phase by current available methods can be challenging. Here we report a convenient method to synthesize peptide C-terminal N-alkyl amides using the well-known Fukuyama N-alkylation reaction on a standard resin commonly used for the synthesis of peptide C-terminal primary amides, the peptide amide linker-polyethylene glycol-polystyrene (PAL-PEG-PS) resin. The alkylation and oNBS deprotection were conducted under basic conditions and were therefore compatible with this acid labile resin. The alkylation reaction was very efficient on this resin with a number of different alkyl iodides or bromides, and the synthesis of model enkephalin N-alkyl amide analogs using this method gave consistently high yields and purities, demonstrating the applicability of this methodology. The synthesis of N-alkyl amides was more difficult on a Rink amide resin, especially the coupling of the first amino acid to the N-alkyl amine, resulting in lower yields for loading the first amino acid onto the resin. This method can be widely applied in the synthesis of peptide N-alkyl amides.
SUBSTITUTED QUINAZOLINE DERIVATIVES AND THEIR USE AS INHIBITORS
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, (2008/06/13)
The use of a compound of formula (I) 1 or a salt, ester or amide thereof; where X is O, or S, S(O) or S(O)2, or NR6 where R6 is hydrogen or C1-6 alkyl,; R5 is an optionally substituted 5-membered heteroaromatic ring, R1, R2 ,R3, R4 are independently selected from various specified moieties, in the preparation of a medicament for use in the inhibition of aurora 2 kinase. Certain compounds are novel and these, together with pharmaceutical compositions containing them are also described and claimed
Ring contraction of 1,4-benzodiazepines to 3,4-dihydroquinazolines during macro scale reduction (example 5: Cyprazepam)
Oelschlager,Martienssen,Belal
, p. 503 - 507 (2007/10/02)
Cyprazepam (1) is reduced in 3 steps with consumption of 6 Θ at the DME as well as at the stirred Hg-cathode. During these processes ring contraction is observed with formation of 6-chloro-2-methyl-4-phenyl-3,4-dihydroquinazoline accompanied by elimination of cyclopropylmethylamine. This is the fifth example of a reductive ring contraction, which occurs only at a Hg-cathode but not during catalytic hydrogenation.
Palladium(II)-Catalyzed Cyclopropanation of Simple Allyloxy and Allylamino Compounds and of 1-Oxy-1,3-butadienes with Diazomethane
Tomilov, Yu. V.,Kostitsyn, A. B.,Shulishov, E. V.,Nefedov, O. M.
, p. 246 - 248 (2007/10/02)
(Alkyloxymethyl)-, (aminomethyl)-, (2-alkoxyethenyl)-, (2-acetoxyethenyl)-, and (2-siloxyethenyl)cyclopropanes are obtained in high yields by reaction of allyl alcohol or derivatives, allylamines, 1-alkoxy-, 1-acetoxy-, and 1-trimethylsiloxy-1,3-butadienes with diazomethane in dichloromethane/diethylether in the presence of bis(benzonitrile)palladium dichloride.
REACTIONS OF DIAZOALKANES WITH UNSATURATED COMPOUNDS. 8. CATALYTIC CYCLOPROPANATION OF ALLYL ALCOHOLS AND ALLYLAMINES WITH DIAZOMETHANE
Tomilov, Yu. V.,Kostitsyn, A. B.,Dokichev, V. A.,Dzhemilev, U. M.,Nefedov, O. M.
, p. 2518 - 2521 (2007/10/02)
Allyl alcohols and allylamines have been cyclopropanated directly with diazomethane in the presence of palladium compounds to give 60-88percent of cyclopropylmethanols and cyclopropylmethylamines, respectively, almost free from the products of formal insertion of methylene into the heteroatom-hydrogen bond.
PHENOXYPROPANOLAMINES
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, (2008/06/13)
Phenoxypropanolamine derivatives are prepared. These compounds have . beta.-adrenergic stimulant activity particularly as selective bronchodilators.
