Diphenyl-morpholino

Dimethyliminiono-cthylidcnc)-diphenyl- 2959 Cyclopropylium Diphenyl-pyrrolidino- 3123 C H NO Cydopropenyliiim Diphenyl-morpholino- 2728. 3123, 3145, 3161, 3167 C.,H 0... 

Furan, 3-(4-methylpentanoyl) — see Perilla ketone Furan, 2-methylthio-mass spectrometry, 4, 583 Furan, 3-morpholino-2,5-diphenyl-reaotions... 

C) Preparation of Doxapram Hydrochloride [3,3-Diphenyl-1-Ethyl-4-(2-Morpholino-Ethylj-2-Pyrrolidinone Hydrochloride Monohydrate] A solution of 25 grams (0.076 mol) of 4-(2-chloroethyl)-3,3-diphenyl-1-ethyl-2-pyrrolidinone and 13.3 grams (0.153 mol) of morpholine in 500 ml of absolute ethanol was heated at 95°-120°C for 21 hours in a closed system and concentrated in vacuo. The residue was dissolved in 3(X) ml of two normal hydrochloric acid and extracted with 150 ml of ethyl acetate. A solid crystallized (13 g) during the extraction and was removed by filtration. MP 217°-219°C. The acid extracts were made basic with sodium hydroxide and extracted with ether, and the ether solution was concentrated in vacuo and the residue was suspended in six normal hydrochloric acid. Additional crystalline product formed and was recrystallized from two normal hydrochloric acid. Yield, 10 grams MP 217°-219°C. Total yield, 23 grams (70%). 

The thermolysis of 4-azidophenyl methyl ketone in morpholine at 170°C yields a mixture of the expected 5-acetyl-2-morpholino-3f/-azepine (33) and 6-acetyl-2-morpholino-3//-azepine (34), the product of a unique and totally unexpected thermal rearrangement of the 5-acetyl derivative.119 Similar results can be obtained in hot piperidine, whereas thermolysis of 4-azido-diphenyl ketone under similar conditions yields only the 6-benzoyl-2-(cycloalkylamino)-3//-azepines (7-18%) accompanied by much tar. 

A mixture of diphenyl-3-(2-morpholino-l-cyclohexenyl)phosphine sulfide (3.25 g, 8.5 mmol) and triethylamine (0.91 g, 9 mmol) in benzene (20 ml) was added to a solution of phosphorus tribromide (2.30 g, 8.5 mmol) in benzene (20 ml). After 2 h, a mixture of methanol (0.55 g, 17 mmol) and triethylamine (1.82 g, 18 mmol) in benzene (20 ml) was added with stirring to the solidified mass. After 1 h, the mixture was filtered, the filtrate was evaporated, and the residue was ground with petroleum ether. There was thus isolated pure dimethyl 3-dip henylthiophosphoryl-2-morpholino-l-cyclohexenylphospho-nous acid of melting point (mp) 193-196°C (3.14 g, 78%). 

Janssen, P.A.J. and Jageneau, A.H. (1957). A new series of potent analgesics Dextro 2 2-diphenyl-3-methyl-4-morpholino-butyrylpyrrolidine and related amides. J. Pharm. Pharmacol. 9 381—400. 

Dimorpholino-phenyl-methan und analoge Aminale reagieren mit Phenyl-ethin in Gegen-wart von Kupfer(I)-halogeniden, vermutlich iiber eine kupferorganische Zwischenstufe, zu l,3-Diphenyl-3-morpholino-propin bzw. analogen Produkten2. 

To a flask which was previously base-washed and dried is added 32 ml of 1.5 M potassium f-butoxide solution in dimethyl sulfoxide. (NOTE The potassium f-butoxide (MSA Research Corp.) is sublimed under 0.1 mm pressure at 155°-160°C, transferred to a brown bottle in a dry nitrogen atmosphere, sealed with a serum cap, dry dimethyl sulfoxide added, and the resulting solution only removed with a syringe.) To the latter solution is added 1.99 gm (0.0046 mole) of the mesitoate ester of < -f/ ra>-2-(4-morpholino)-l, 2-diphenyl-ethanol, the reaction is stirred for 3 hr at room temperature under a nitrogen atmosphere, and the mixture poured in 150 ml of ice-cold water. The resulting solution is extracted with ether, dried, and concentrated to afford 1.16 gm (94%) of crude enamine, m.p. 78°-81°C. The enamine is dissolved in the minimum amount of methanol at temperatures below 50°C, quickly cooled, and then filtered to afford 0.79 gm (65%), m.p. 103°-104°C. 

Reaction of 1-bromo- and l-chloro-2-(4-morpholino)-l,2-diphenyl-ethene with phenyllithium in benzene to give 2-(4-morpholino)-l,2-diphenyl-ethene [202]. 

Moramide-Intermediate, 2-methyl-3-morpholino-l, 1-diphenyl-propane-carboxylic acid. 

The adduct 32 of diphenylcyclopropenethione to the morpholine enamine of acetophenone reacts with dimethyl acetylenedicarboxylate to yield a mixture of 1,2-diphenyl cyclopropene and dimethyl 4-morpholino-3-phenylthiophene-1,2-dicarboxylate (equation 21)41. 

Diphenyl-5-hydroxy-l-methoxy-carboiiyl-5-methyl-3-morpholino-3167... 

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