Morpholine derivatives

Amorolfine [78613-35-17 is a molecule that is totally different from this group it is a morpholine derivative (15) (19). This substance has a broad-spectmm activity and has a fungicide effect at fairly low concentrations. The development of a nail varnish for treatment of onychomycoses could be very interesting. 

Diaminobiphenyl Derivative, 698 /7-Propylamine and /-Propylamine Derivatives, 699 /V,/ /-Dimethyl-(f ,/ )-1,2-diaminocyclohexyl, 699 Morpholine Derivative, 699... 

In much the same vein, the basic ester 7 can be obtained by reaction of the same chloroacid with morpholine derivative 6. Reaction with aniline 4 affords mornif1umate (8). 

Yet another nontricyclic antidepressant consists of a relatively simple morpholine derivative. Acylation of aziridine with p-chlorobenzoyl chloride gives the amide 130. This intermediate is. sufficiently reactive to undergo ring opening on treatment with morpholine. The product is the antidepressant agent moclobemide (131) 33J. 

Vinylamide morpholine derivative acrylic acid copolymer [1773]... 

A morpholine derivative is active as a muscle relaxant. To prepare it, reaction of arylphenethanol-amine derivative 164 with sodium hydride and ethyl... 

The ylide obtained from (methyl)triphenylphosphonium bromide reacts with morpholine derivatives 597 to give phosphonium salts 598 which upon treatment with -butyllithium are converted to new ylides 599. In a reaction with aldehydes, ylides 599 form iV-(l,3-disubstituted allyl)-morpholines 602 (Scheme 94) <1996AQ138>. Another less common nucleophile that can be used for substitution of the benzotriazolyl moiety in Af-(a-aminoalkyl)benzotriazoles is an adduct of iV-benzylthiazolium salt to an aldehyde which reacts with compounds 597 to produce adducts 600. Under the reaction conditions, refluxing in acetonitrile, salts 600 decompose to liberate aminoketones 601 <1996H(42)273>. 

Krupp-Koppers (2) A process for separating butane and butene isomers from their mixtures by extractive distillation. The added solvent (Butenex) is a morpholine derivative, possibly N-formyl morpholine. 

I Brand Name(s) Analpram-HC, Anusol, Enzone, Epifoam, Itch-X, Pramosome, Prax, ProctoCream, ProctoFoam NS, Rectocort, Tronolane, Zone-A Chemical Class Morpholine derivative... 

The use of 3 also allows for [3 + 2] cycloaddition with enaminoketones (38) (Scheme 8.3). When the morpholine-derived enaminoketon 6 was used, a mixture of A -pyrazoline 7 and pyrazole 8 was obtained. Complete transformation of 7 into 8 was achieved by treatment with water. In the case of the pyrrohdine-derived enaminoketone 9, pyrazole 11 and diazabicycloheptadiene 10 are formed competitively. In the formation of the latter compound, reaction of a second equivalent of 3 with the carbonyl group of 9 is involved. Reaction of uracil as... 

Further transformations of a-alkyl-3-oxazolidineacetonitriles are possible. Addition of methyllithium to the cyano group followed by acid hydrolysis gave a morpholine derivative, from which a /i-amino alcohol was obtained as a diastereomeric mixture (d.r. 80 20)69. 

Meinert et al. have also studied the electrochemical fluorination of piperidine-, carbazole-, and morpholine-derivatives [85,86]. The perfluoro-derivatives were said to be produced in yields up to 45 %, with the fluorination of N-carbazoles representing a new class of compounds. 

The morpholine derivatives phenmetrazine (173 R = H) and phendimetrazine (173 R = Me) have stimulant properties like those of amphetamine. They have been used as anorectics, but they are liable to abuse. Another CNS stimulant used as an anorectic is mazindol (174), which bears some resemblance to certain benzhydrols with antidepressant activity. 

Suntomchashwej S, Chaichit N, Isobe M, Suwanborirux K (2005) Hectochlorin and Morpholine Derivatives from the Thai Sea Hare, Bursatella leachii. J Nat Prod 68 951... 

Asymmetric conjugate addition of a-substituted-oc-cyanoacetates 77 to acetylenic esters under phase-transfer conditions is somewhat of a challenge, because of the difficulty encountered in controlling the stereochemistry of the product. In addition, despite numerous examples of the conjugate additions to alkenoic esters, no successful asymmetric conjugate additions to acetylenic esters have been reported to date. In this context, Maruoka and coworkers recently developed a new morpholine-derived phase-transfer catalyst (S)-76 and applied it to the asymmetric conjugate additions of a-alkyl-a-cyanoacetates 77 to acetylenic esters, as indicated in Table 5.11 [40], In this asymmetric transformation, an all-carbon quaternary stereocenter can be constructed with a high enantiomeric purity. 

Sucrose was also used as starting material for the preparation of morpholine derivatives. The first step involved a controlled oxidation of either ring of sucrose (Scheme 23).173... 

Ergosterol biosynthesis inhibitors differ in their molecular modes of action. This is especially true for the morpholine derivative tride-morph and fenpropimorph. In Pyricularia oryzae, tridemorph inhibits the A to A7 -isomerization reaction in ergosterol synthesis,... 

The morpholine derivative 75 has an obvious amide disconnection to 76 and a less obvious 1,2-diX disconnection at the ether to 77. This is obviously an epoxide 78 adduct with ammonia. 

An interesting transformation has been reported by Burlingham and Widlanski <2001JA2937>, who synthesized fused-ring thietane-1,1-dioxide 115, in 38% yield, by the reaction of iV-benzyl dimethyldisulfonimide 113 with the morpholine derivative 114 in the presence of butyllithium (Equation 33). 

This oxidative chlorination-cyclization strategy has also been applied to the synthesis of the bicyclic /3-sultam 166 from chiral morpholine derivatives (Scheme 51) <2004HCA90>. 

The readily available methyl 3,3-dimethylcyclopropene-l-carboxylate (III/54) undergoes [2+2] cycloaddition with enamines e.g. the morpholine derivative III/55 to give 2-aminobicyclo[2.1.0]pentane derivatives, e.g. III/56. These compounds are transformed into cyclopentane derivatives, e.g. methyl 4-hydroxy-2,5,5-trimethyl-1-cyclopentenecarboxylate (III/57) by treatment with dilute mineral acids. 

The rates of hydrolysis of compounds 12 (X = H), 13 and 14 are independent of pH from about pH 6 to 1, and buffer catalysis is not seen. The interpretation of these results is the same as it is for series 5, namely rate-controlling attack by water on the iminium ion. At these pH values the enamine is present in a protonated form and equation 23 is the rate law. As is clear from Figure 2, the morpholine-derived iminium ion is by far the most electrophilic, while the pyrrolidino iminium ion is least reactive. This order is exactly the same as for compounds 1-3 the reasons were discussed in Section III.A.2. Rate constants for nucleophilic attack upon the iminium ions are given in Table 8. 

Description In the extractive distillation (ED) process, a single-compound solvent, N-Formylmorpholine (NFM), or NFM in a mixture with further morpholine derivatives, alters the vapor pressure of the components being separated. The vapor pressure of the olefins is lowered more than that of the less soluble paraffins. Paraffinic vapors leave the top of the ED column, and solvent with olefins leaves the bottom of the ED column. 

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