3-Butyl-4-phenyl- -Hydrochlorid

Fexofenadine hydrochloride (1, ( )-2-[4-]-lhydroxy-4-(hydroxydiphenylmethyl)-l-piperidino]butyl]phenyl]-2-methylpropanoic acid, Allegra ) is an antihistamine agent, acting as an Hi antagonist. 

In the Sepracor synthesis of chiral cetirizine di hydrochloride (4), the linear side-chain as bromide 51 was assembled via rhodium octanoate-mediated ether formation from 2-bromoethanol and ethyl diazoacetate (Scheme 8). Condensation of 4-chlorobenzaldehyde with chiral auxiliary (/f)-f-butyl sulfinamide (52) in the presence of Lewis acid, tetraethoxytitanium led to (/f)-sulfinimine 53. Addition of phenyl magnesium bromide to 53 gave nse to a 91 9 mixture of two diastereomers where the major diasteromer 54 was isolated in greater than 65% yield. Mild hydrolysis conditions were applied to remove the chiral auxiliary by exposing 54 to 2 N HCl in methanol to provide (S)-amine 55. Bisalkylation of (S)-amine 55 with dichlonde 56 was followed by subsequent hydrolysis to remove the tosyl amine protecting group to afford (S)-43. Alkylation of (5)-piperizine 43 with bromide 51 produced (S)-cetirizine ethyl ester, which was then hydrolyzed to deliver (S)-cetirizine dihydrochloride, (5)-4. 

A stirred mixture of 9.9 g (0.03 mole) of l-[4,4-(di-p-fluorophenyl)butyl]piperazine, 5,0 g (0,03 mole) of phenyl N-ethylcarbamate, 6,6 g of potassium carbonate and 100 ml of toluene was heated at reflux for 45 minutes. The mixture was filtered and the solvent was removed. The residual oil was dissolved in ethanol-ether and the hydrochloride was precipitated with hydrogen chloride in ethanol. The solid was collected by filtration and recrystallized from 2-butanone-isopropanol 4 1 to give 6.8 g of N -ethyl-4-[4,4-(di-p-fluorophenyl)butyl]-l-piperazinecarboxamide hydrochloride. Melting point 177-178°C. 

D) 4 -[N-Ethyl-l"-Methyl-2"-(4" -Methoxyphenyl)Ethylamino]Butyl-3,4-Dimethoxybenzoate Hydrochloride 10.3 g of 4 -iodobutyl-3,4-dimethoxybenzoate and 11.0 g of N-ethyl-p-methoxyphenylisopropylamine (obtained by catalytic reduction of an alcoholic solution of an excess quantity (60%) of p-methoxy-phenyl-acetone, to which was added a 33% (weight-for-... 

To a mixture of 4.2 g (0.0083 mole) of 4 -tert-butyl-4-[4-(a-hydroxy-a-phenylbenzyl)piperidino]-butyrophenone hydrochloride and 0.54 g (0.01 mole) of sodium methoxide in 25 ml of methanol is added 2.16 g (0.04 mole) of potassium borohydride. The reaction mixture is stirred overnight, diluted with water and the methanol removed under reduced pressure. The remaining material is extracted with chloroform, washed with water, dried over magnesium sulfate and filtered. The filtrate is concentrated, and the residue is recrystallized from acetone-water to give 4-[a-(p-tert-butylphenyl)-a-hydroxybenzyl]-a-phenyl-l-piperidinebutanol, melting point 161°-163°C. 

Other Organic Compounds aniline hydrochloride benzyl hydroperoxide butyl chloride dicyclohexyl peroxide diethyl sulfide methyl iodide 2-naphthoyl bromide sodium S-phenyl thiosulfite fert-butyl fluoride... 

Aniline hydrochloride Benzyl hydroperoxide Butyl chloride Dicyclohexyl peroxide Diethyl sulfide Methyl iodide 2-Naphthoyl bromide Sodium S-phenyl thiosulfite ferf-Butyl fluoride... 

Robison, and Robison were the first to prepare 7-azagramine (3-dimethylaminoniethyl-7-azaindole), finding the following procedure to give optimum yields. The azaindole, 10% excess dimethyl-amine hydrochloride, and one molar equivalent of paraformaldehyde are refluxed together in w-butanol for 30 minutes, followed by evaporation under reduced pressure. The residue is extracted with dilute acid, from which the base is precipitated with sodium carbonate. This procedure has been used with only minor variations on a variety of 7-azaindoles. Williamson obtained 7-azagramine in 99% yield on a 0.2-mole scale, compared to 81%. Other 7-azagramines prepared similarly are l-phenyl-4-methyl (72%), ° l-butyl-4-methyl (64%), 6-chloro-4-methyl (60%), 4-methyl (28%), 2-methyl, and 5-methyl (60%). In the case of the last two 4-methyl compounds, it was found that the best yields were obtained with use of a 3 1 molar ratio of dimethylamine hydrochloride and only a 15-minute reflux period. With the 6-chloro-4-methyl isomer, some (6%) of the bis-(7-aza-3-indolyl)methylene by-product was formed. 

Mepben(ermine. N,a,a-Trimethylbenzeneethan-omine N, , trimethylphtnelhylamine 2-methylamino-2--methyl-1 -phenylpropane JV-methyl- -phenyl-lert-butyl. amine Wyamine Vial in Mephine. C H, N mol wt 163,25. C 8092%, H 10.50%. N 8,58%. Prepd by hydrogenating 1 -chloro-2 -methylamino-2-methyl- ]. phenyipropane hydrochloride in methanol in the presence of palladium barium carbonate Bruce, Szabo, U,S, pat. 2,597,445 (1952 to Wyeth). Alternate process Abel et at, US. pat. 2,890,079 (1952 to Wyeth). 

It may be prepared by the interaction of (4- er -butyl-2, 6-dimethyl-phenyl) acetonitrile with ethylenediamine hydrochloride at an elevated temperature with the loss of a mole of ammonia. 

ID) 4 -[N-Ethyl-l"-Methyl-2"-(4" -MethoxyphenyllEthylamino]Butyl-3,4-Dimethoxyben-zoate Hydrochloride 10.3 g of 4 -iodobutyl-3,4-dimethoxybenzoate and 11.0 g of N-ethyl-p-methoxyphenylisopropylamine (obtained by catalytic reduction of an alcoholic solution of an excess quantity (60%) of p-methoxy-phenyl-acetone, to which was added a 33% (weight-for-weight) aqueous solution of ethylamine, with Pt as a catalyst), were boiled in 200 ml of methyl ethyl ketone for 20 hours, cooled and the iodine ion was determined the reaction was found to be complete. Then the methyl ethyl ketone was evaporated in vacuo and the residue was dissolved in 300 ml of water and 30 ml of ether the layers were separated and the water layer was extracted twice more with 20 ml portions of ether. 

Reofos TPP. See Tri phenyl phosphate Reolube TBEP. See Tributoxyethyl phosphate Reoiube TBP. See Tri butyl phosphate Reoiube TOP. See Trioctyl phosphate Reomoi TBP. See Tributyl phosphate Reomoi TOP. See Trioctyl phosphate Reomoi TPP. See Tri phenyl phosphate Repak. See Calcium hypochlorite Replay RP 2177. See Polystyrene, high-impact Replay RP 2236. See Polystyrene Repolem . See Acrylic resin Reputex 20. See Poly (hexamethylenebiquanide) hydrochloride Reserve Salt Flake. See Sodium m-nitrobenzenesulfonate Residue gas. See Natural gas... 

Nuclear magnetic resonance spectroscopy has been used to study self-ossociation in promethazine hydrochloride, in 2-butyl-3-benzofuranyl 4-[2-(diethylamino) ethoxy]-3,5-diiodo-phenyl ketone hydrochloride (SKF 33134A),40ond in d-propoxyphene hydrochloride. Florence has measured the properties of p-diethylaminoethyl diphenylpropylacetate hydrochloride (SKF 525-A) by light scattering, surface tension, and microelectrophoretic techniques. He suggests that caution should be exercised in the interpretation of enzyme inhibition results obtained with a compound of this type since it exhibits surface activity, and surfactants are known to exert an appreciable effect on certain enzyme systems. 

C2 8H2i B2F8Ni,S, 3,3 -Thiobis- (2-methyl--1 -phenyl imidazo- [ 1,5-a ]pyr id-inium) bistetrafluoroborate, 46B, 266 C2 8H2 8CIF2N3O, 1 -(1-(4,4-Bis(4-fluorophenyl)butyl)-4-piperidinyl)-5-chloro-1, 3-dihydro-2H-benzimidazol-2-one, 43B, 353 C28H30CIF2N3O, 1- 1-[4,4-Bis(4-fluorophenyl)butyl]-4-piperidyl -2-benzimidazolinone hydrochloride, 45B, 288 C28H30CIF2N3O5, Pimozide perchlorate, 45B, 288 C2 8H5 eBr 16NflSb2, Quinuclidinium dodecabromoantimondll )antimon-(V)ate-2-dibromine, 37B, 678... 

The poly-thio-A -/ -A -(methyl-aminomethyl)-ethylenes are amorphous and stereoirregular, in contrast to polypropylene sulfide obtained with the same initiator, which is highly crystalline but it should be mentioned that one of the asymmetric centers is in the lateral chain and not in the main chain, as it is in propylene sulfide. Optical rotatory dispersion curves are independent of the polymerization conditions, they are complex for poly-thio-A -sec-butyl-A -methylaminomethyl-ethylene in different solvents and simple for poly-thio-A -methyl-A -(phenyl-l-ethyl)-aminomethyl ethylene. The ORD s of the poly-hydrochlorides of both polymers in water are normal but quite different from those of the polyamines. The OA polybases are soluble, when protonated, in strongly acidic media. By addition of dioxane or, better, acetonitile, the polybases remain soluble even for a degree of deprotonation of 45% [112]. By an irreversible methylation by dimethyl-sulfate (>10%), the polybases become water-soluble. The chiroptical properties permit the following conclusions ... 

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