4441-34-3

Basic information

• Product Name: r-[2-(4-morpholinyl)ethyl]-
• CAS NO: 4441-34-3
• Molecular Weight: 221.299
• Mol File: 4441-34-3.mol

Chemical Properties

• CAS DataBase Reference: r-[2-(4-morpholinyl)ethyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: r-[2-(4-morpholinyl)ethyl]-(4441-34-3)
• EPA Substance Registry System: r-[2-(4-morpholinyl)ethyl]-(4441-34-3)

Safety Data

• Hazardous Substances Data: 4441-34-3(Hazardous Substances Data)

Upstream product

• 98-86-2 acetophenone 
• 110-91-8 morpholine 
• 62872-58-6 3-iodo-1-phenyl-propan-1-ol 
• 25039-19-4 (E)-3-morpholino-1-phenyl-2-propen-1-one 
• 93-54-9 1-Phenyl-1-propanol 
• 936-59-4 3-chloropropiophenone 
• 18776-12-0 3-chloro-1-phenyl-propan-1-ol 
• 4393-06-0 1-Phenyl-2-propen-1-ol 
• 2298-48-8 3-morpholin-4-yl-1-phenyl-propan-1-one 
• 4436-23-1 2-phenyloxetane 
• 1020-16-2 3-morpholino-1-phenylpropan-1-one hydrochloride 

Downstream Products

• 14611-98-4 N-(3-morpholin-4-yl-1-phenyl-propyl)-acetamide 
• 25901-61-5 4-(3-hydroxy-3-phenyl-propyl)-morpholin-3-one 
• 173366-49-9 1-chloro-3-morpholino-1-phenylpropane 
• 26409-35-8 3-(4-oxy-morpholin-4-yl)-1-phenyl-propan-1-ol 
• 1384515-34-7 2-phenylhexahydro-2H-[1,3]oxazino[2,3-c][1,4]oxazine 
• 157846-75-8 4-[3-(3,4-Dimethoxy-phenoxy)-3-phenyl-propyl]-morpholine 
• 157846-72-5 4-[3-(2-Methoxy-phenoxy)-3-phenyl-propyl]-morpholine 
• 157846-73-6 4-[3-(3-Methoxy-phenoxy)-3-phenyl-propyl]-morpholine 
• 157846-74-7 4-[3-(4-Methoxy-phenoxy)-3-phenyl-propyl]-morpholine 
• 157846-71-4 4-(3-phenoxy-3-phenyl-propyl)-morpholine 
• 157846-66-7 Methanesulfonic acid 3-morpholin-4-yl-1-phenyl-propyl ester 

Relevant articles and documents

Manganese-Catalyzed Anti-Markovnikov Hydroamination of Allyl Alcohols via Hydrogen-Borrowing Catalysis

Controlling the selectivity in a hydroamination reaction is an extremely challenging yet highly desirable task for the diversification of amines. In this article, a selective formal anti-Markovnikov hydroamination of allyl alcohols is presented. It enables the versatile synthesis of valuable γ-amino alcohol building blocks. A phosphine-free Earth's abundant manganese(I) complex catalyzed the reaction under hydrogen-borrowing conditions. A vast range of aliphatic, aromatic amines, drug molecules, and natural product derivatives underwent successful hydroamination with primary and secondary allylic alcohols with excellent functional group tolerance (57 examples). The catalysis could be performed on a gram scale and has been applied for the synthesis of drug molecules. The mechanistic studies revealed the metal-ligand bifunctionality as well as hemilability of the ligand backbone as the key design principle for the success of this catalysis.

Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols

Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.

A formal anti-Markovnikov hydroamination of allylic alcohols via tandem oxidation/1,4-conjugate addition/1,2-reduction using a Ru catalyst

A formal anti-Markovnikov hydroamination of allylic alcohols using a Ru catalyst via tandem oxidation/1,4-conjugate addition/1,2-reduction was developed. Thus, the reaction of allylic alcohols with amines was performed in the presence of the catalyst generated from RuClH(CO)(PPh3)3 and 2,6-bis(n-butyliminomethyl)pyridine in situ to afford the corresponding γ-amino alcohols efficiently. This journal is

Synthesis and antimicrobial activity of some new 1,2,4-triazine and benzimidazole derivatives

1-(4-Substituted phenyl)-3-(substituted)propan-1-(1H-benzo[d]imidazol-2-yl) hydrazines and 1-(4-substituted phenyl)- 3-(substituted)propan-1-(5H-[1,2,4] triazino[5,6-b]indol-3-yl) hydrazines have been synthesized by the fusion of triazine and benzimidazole derivatives with Mannich bases. The synthesized compounds have been characterized and screened against ITCC 5226 Sclerotium rolfsii and ITCC 0482 Macrophomina phaseolina and MTCC739 Escherichia coli, ATCC6533 Bacillus subtilis, ATCC9144 Staphylococcus aureus, ATCC25619 Pseudomonas aeruginosa and ATCC24433 Candida albicans.

Electrooxidative cyclization of hydroxyamino compounds possessing a benzyl group

Several novel 2-aryl-1,3-oxazinane and 2-aryl-1,3-oxazolidine derivatives were synthesized from N-benzyl-2-piperidineethanols and N-benzyl-2- piperidinemethanols, respectively, by using electrooxidative methods in methanol. For these reactions, the yields of the corresponding cyclized compounds were significantly increased by using catalytic amounts of iodide ions. In contrast, 3-dialkylamino-1-phenylpropanols afforded the expected cyclic 6-phenyl-1,3-oxazinane derivatives using only a small excess of base. Georg Thieme Verlag Stuttgart · New York.

Simplified heterocyclic analogues of fluoxetine inhibit inducible nitric oxide production in lipopolysaccharide-induced BV2 cells

A series of fluoxetine, where the N-methylamino group was replaced and then simplified, were synthesized and their inhibitory effect was tested for nitric oxide (NO) production and inducible NO synthase (iNOS) expression in lipopolysaccharide (LPS)-induced BV2 cells. Although the synthesized compounds generally revealed weaker activity or greater cytotoxicity than fluoxetine, compound 10a, in which the N-methylamino group in fluoxetine was replaced by morpholine, and the trifluoromethylphenyl ring was substituted with simple oxo group, suppressed NO production dose-dependently at 10, 20 and 40 μM concentrations with less cytotoxicity than fluoxetine, and inhibited iNOS mRNA and protein expression at the same concentrations in LPS-induced BV2 cells. The results suggested that the trifluoromethylphenyl ring moiety in fluoxetine is not necessary for the suppression of NO production and that 10a has the potential as a potent inhibitor of NO production.

Transformation of α-substituted propanols into γ-amino alcohols through nickel-catalyzed amination on the terminal γ-carbon of propanols

A nickel-phosphine complex was found to be effective as the catalyst for the transformation of alcohols into β-enaminones, which was successively converted into γ-amino alcohols by a conventional reductant. The sequential transformation is equivalent to the carbon-nitrogen bond formation at the γ-position of saturated alcohols. Georg Thieme Verlag Stuttgart · New York.

Propanolamine derivatives, their preparation and use

Compounds of formula I wherein, X is phenyl unsubstituted or optionally substituted with one or more cyano, halogeno, halogenoalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkenyl, aryloxy, aralkoxy, amino, C1-6-alkyl mono or disubstituted amino, C1-4-alkanoylamino, carbamoyl, C1-4-alkyl N-mono or disubstituted carbamoyl, C1-4-alkyl substituted with amino, C1-2-alkyl mono or disubstituted amino, N02, morpholino or imidazolyl; and, R is 3,4-methylenedioxyphenyl, aryl or heteroaryl all of which can be optionally substituted with one or more cyano, halogeno, C1-6-alkyl, C1-6-alkoxy, C2-6-alkenyl, trifluoromethyl, C3-5-alkylene, aryloxy, aralkoxy or C1-6-alkylthio; and, R1 and R2 are C1-10-alkyl, C3-7-cycloalkyl, C2-10-alkenyl, C3-6-cycloalkyl-C1-5-alkyl, all of which can be unsubstituted or substituted with C1-5-alkyl, C1-5-alkoxy or cyano; or, R1 and R2 together form a 5, 6 or 7 membered ring containing at least one nitrogen atom, or which optionally contains two nitrogen atoms, one or two oxygen atom(s) or one or two sulphur atom(s) or a combination thereof, which ring is unsubstituted or optionally substituted with C1-4-alkyl, C1-4-alkoxy or aryl; and, R3, R4, R5, R6, and R7 independently are hydrogen, C1-4-alkyl or phenyl; or, R4 and X together form a carbocyclic ring containing 5 or 6 atoms, or a salt thereof with a pharmaceutically acceptable acid; provided however that R1 and R2 are not C3-7-cycloalkyl, C1-10-alkyl or C2-10-alkenyl which may be straight, branched or cyclic, unsubstituted or substituted with C1-4-alkoxy, aryloxy or cycloalkyl, cyano or cycloalkylalkyl, when X is phenyl substituted with cyano, halogen, halogenalkyl, C1-6-alkoxy, C1-6-alkyl, C1-5-alkanoyl, C3-5-alkylene, aryloxy or aralkoxy, are useful in the treatment of anoxia, traumatic injury, ischemia, migraine, epilepsy, Parkinson's disease, Alzheimer's disease and other neurodegenerative diseases.

Synthesis of 3-aryloxy-3-phenylpropanamines as possible antidepressants

Thirteen new 3-aryloxy-3-phenylpropanamines (11-23) have been prepared and their structures elucidated by mass, IR and 1H-NMR spectra and by elemental analysis.Being structurally similar to fluoxetine these compounds have been tested for their effect on g

Aminolysis of Oxetanes: Quite Efficient Catalysis by Lanthanide(III) Trifluoromethansulfonates

Ln(III)trifluoromethansulfonates in CH2Cl2 efficiently catalyze the aminolysis of trimethylene oxide, 2-octyl-, and 2-phenyloxetane, at r.t., to give the corresponding γ-amino alcohols in very good yields.