Morpholine 4-benzyl

The morpholine-benzyl, phenyl isoxazole is the Murcko framework for this bioactive molecule. 

Tosyl azide reacts differently to give sulfonamide derivatives 134). The morpholine enamine from dibenzylketone (196) for instance reacted with tosylazide to give 197 and phenyldiazomethane (198), which was trapped with acetic acid giving benzyl acetate 134). 

A solution of 1-benzyl-4-piperidone, ethyl cyanoacetate, powdery sulfur and morpholine in ethanol is heated moderately under reflux for about 20 minutes to dissolve the powdery sulfur. The mixture is heated under reflux for one further hour to complete the reaction. On standing at room temperature, the mixture yields a precipitate. The precipitate is collected by filtration, washed well with methanol and recrystallized from methanol to give 2-amino-6-benzyl-3-ethoxycarbonyl-4,5,6,7-tetrahydrothieno(2,3-c)-pyridine as almost colorless needles melting at 112° to 113°C. 

Hydroxy-4-benzyl-5,6-diphenyl-2,3-dihydro-1,4-oxazin wird durch Lithiumalanat iiber das Enol-Salz zu 2-Hyclroxy-4-benzyl-2,3-diphenyl-morpholin reduziert6. Durch Ringoffnung und Schliefiung wird die Hydr-oxy-Gruppe verschoben. 

DE 3 540 093 (Farmitalia Carlo Erba appl. 12.11.1985 GB-prior. 22.11.1984). configurational studies on 2-la-(2-ethoxyphenoxy)benzyl]morpholine ... 

JV -Benzyloxycarbonyl-0-tert-butyl-L-serine Alanine, 3-tert-butoxy-N-carboxy-, Ai-benzyl ester, l- (8) L-Serine, 0-(l,l-dimethylethyl)-N-[(phenylmethoxy)carbonyl]- (9) (1676-75-1) Morpholine, 4-methyl- (8, 9) (109-02-4)... 

The asymmetric synthesis of 2,3-diamino acids can be accomplished by the addition of chiral enolates to prochiral imines. For example, reaction of morpholine-2-one 103, derived from (S)-phenylglycinol, with N-benzyl ben-zaldimine in the presence of pyridine and para-toluenesulfonic acid at high... 

Y )- Benzyl morpholine is a potent appetite suppressant drug. The synthesis of 2-(/ )-benzyl-morpholine began with the reduction of the unsaturated bromocinnamaldehyde to the corresponding saturated (X)-bromo-alcohol by baker s yeast, with a very low ee of 63%. However, an efficient transformation can be achieved by controlling the substrate concentration with the addition of hydrophobic resin Amberlite XAD-1180 [26]. With a resin-to-substrate ratio of one and an initial substrate concentration of 5 gL, the saturated (X)-bromo-alcohol was recovered at nearly quantitative yield and 98.6% ee. 

The Pyoc group is stable to acids and bases, but may be selectively removed after conversion into the jV-methylpyridinium form and subsequent treatment with morpholine, to give 146. Treatment of 146 with acetic anhydride in pyridine gave 147. Hydrogenolysis of the benzyl ester group of 147 followed by methanolysis catalyzed by hydrazine afforded (44,73) the de-protected derivative 148. 

The Mannich reaction of secondary amines R NH (dibenzylamine, piperidine, morpholine, etc.), aldehydes R2CHO (R2 = alkyl, Ph or 2-furyl) and thiols R3SH (R3 = alkyl, Ph or benzyl) results in a-amino sulphides, which react with Grignard compounds to give tertiary amines in good yields (equation 47)136. 

Biuret triisocyanate-adduct of hexamethylene diisocya- Mobay Chem. Co. nate with water Dibutyltin dilaurate Dimethyl 2,5-bis(ethyl-hexanoyl peroxy)hexane Benzoyl peroxide Calcium naphthenate Lead naphthenate Cobalt naphthenate Zinc naphthenate N-benzyl-N,N,dimethylamine Copper chloride Ferric chloride N,N-(Dimethylaminoethyl)-morpholine -Caprolactone Hydorquinone Xylene... 

The protected O-glycosyl amino acid ester or O-glycosyl peptide ester (1 mmol) is stirred in morpholine (10 mL) or morpholine-dichloromethane (1 1) for 30 min. After addition of dichloromethane (100 mL), the solution is washed with diluted aqueous acid (citric acid or HC1 pH 4, 50 mL) and with water (4 x 50 mL), dried with NajSO, and concentrated in vacuo. The crude product is dissolved in 2-5 mL of ethyl acetate. During chromatography on silica gel (50 g) with petrolum ether ethyl-acetate (2 1), W-(9-fluorenylmethyl)morpho-line is eluted. Subsequently, the deblocked amino acid or peptide ester is eluted with methanol. 0-(2,3,4-Tri-0-benzoyl-(3-D- xylopyranosyl)-L-serine benzyl ester 14 yield, 0.63 g (98%) mp 55°C [a]D —41.4 (c 0.5, CH3OH). IV-(L-Asparaginyl-L-leucyl-)-0-(2,3,4,-0-benzoyl-(3-D-xylopyranosyl)-L-serine benzyl ester 17 yield, 0.85 g (98%) amorphous [a]D —42.3° (c 0.5 CH3OH). 

Amino alcohols Azidotrimethylsilane, 24 Benzyl isocyanate, 30 Diethylamine, 312 Morpholine, 14 Pyrrolidine, 14... 

Regioselective silylcarbonylation of enamines (305) with HSiEt2Me is promoted by [Rh(CO)2Cl]2, giving o -(siloxymethylene)amines (306) as a E/Z mixture (E/Z = 51/49-84/16) in modest to high yields, which are readily hydrolyzed to afford a-siloxyketones (307) (equation 114)313. Enamines of morpholine give much better results than those of diethylamine or benzyl(methyl)amine in this reaction. 

N-Benzyl-2-bromo-N-methyl-benzamide (35). A suspension of morpholine resin (3, 0.63 mmol) in DCM (2 ml) was treated with. V-methyl-benzylamine (0.23 mmol) and 2-bromobenzoyl chloride (0.146 mmol). The reaction mixture was shaken for 5 h. Isocyanate resin (15, 0.2 g) was added followed by DCM (1 ml). The reaction mixture was then shaken for 16 h. Filtration of the resin followed by concentration of the filtrate gave the purified product. 

Chemical Name ()-(2R )-2-((aR )-a-(o-ethoxyphenoxy)benzyl)morpholine, monomethanesulfonate... 

To 2-[a-(2-ethoxyphenoxy)benzyl]-morpholin-3-one in 60 ml of anhydrous THF there was added dropwise under stirring a solution of BH3 in THF. The whole was heated at reflux for 3 hours and dropwise addition under cold conditions (0-(-5)°C) was then made of 3 ml of methanol and then of 3 ml of 23% HCI. The solvent was removed under reduced pressure. The residue was... 

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). 

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