Aminopropyl

ALKANOLAMNES - ALKANOLAMINES FROM OLEFIN OXIDES AND AL ONIA] (Vol 2) (3-(2-Aminoethyl)aminopropyl)trimethoxy silane... 

In most cases, the proteia is immobilized onto y-aminopropyl sUica and covalently attached usiag a cross-linking reagent such as -carbonyl diimidazole. The tertiary stmcture or three dimensional organization of proteias are thought to be important for their activity and chiral recognition. Therefore, mobile phase conditions that cause proteia "deaaturatioa" or loss of tertiary stmcture must be avoided. 

Sugar analysis by hplc has advanced greatly as a result of the development of columns specifically designed for carbohydrate separation. These columns fall into several categories. (/) Aminopropyl-bonded siHca used in reverse-phase mode with acetonitrile—water as the eluent. (2) Ion-moderated cation-exchange resins using water as the eluent. Efficiency of these columns is enhanced at elevated temperature, ca 80—90°C. Calcium is the usual counterion for carbohydrate analysis, but lead, silver, hydrogen, sodium, and potassium are used to confer specific selectivities for mono-, di-, and... 

Other methods of generating a-aminoketones in situ are common, if somewhat less general than the methods already described. 2-Nitrovinylpyrrolidine, which is readily available, yields 2,3-bis(3-aminopropyl)pyrazine on reduction and this almost certainly involves ring opening of the intermediate enamine to an a-aminoketone which then dimerizes under the reaction conditions (Scheme 59) (78TL2217). Nitroethylene derivatives have also served as a-aminoketone precursors via ammonolysis of the derived epoxides at elevated temperatures (Scheme 60) (76S53). Condensation of 1,1-disubstituted hydrazine derivatives with a-nitro-/3-ethoxyethylene derivatives has been used in the synthesis of l,4-dialkylamino-l,4-dihydropyrazines (Scheme 61) (77S136). 

Pyrazine, 3-benzyl-2,5-dihydroxy-6-methyl-cycloaddition reactions, 3, 174 Pyrazine, 2,3-bis(3-aminopropyl)-synthesis, 3, 186... 

Amino-l-phenylbutan-l-ol [a (a-aminopropyl)benzyl alcohol] [( )-threo 5897-76-7] M 165.1, m 79-80 , pK jt -9.7. Crystd from benzene/pet ether. 

Spermine 4HC1 (7V,7V-bis(3-aminopropyl)-l,4-butanediamine 4HC1) [306-67-2] M 348.2, m 313-315". The pKs are similar to spermidine above. Purification as for spermidine trihydrochloride above. 

Dime thy laminopropy I )-3-ethylcarbodiimide hydrochloride [l-ethyl-3-(3-dimethyl-aminopropyl) carbodiimide hydrochloride] see entry on p. 212 in Chapter 4. 

Of the fourth pair, ergoraetrine was found by Jacobs and Craig to yield lysergic acid and cZ- -arainopropyl alcohol (Z-(-l-)- -aminopropyl alcohol), and the same products were obtained by Smith and Timmis 1 from its isomeride, ergometrinine. This pair of alkaloids mxist therefore be hydroxywopropylamides of lysergic acid. The first member of each... 

These hydrazides on treatment with nitrous acid are converted into azides, which with appropriate amino-alcohols, furnish ergometrine and its isomerides and analogues. The four pairs of stereoisomeric ergo-metrines and ergometrinines in the following list have been prepared in this way with l-( -(-)-)S-aminopropyl alcohol or its d-( —)-isomeride. 

The propanolamine obtained by hydrolysis of ergometrine and ergometrinine is dextrorotatory, but belongs to the I- series and appears to be fully described as Z-(-)-)- 3-aminopropyl alcohol. 

Zebiihr et al. (29) developed an automated system for determining PAHs, PCBs and PCDD/Fs by using an aminopropyl silica column coupled to a porous graphitic carbon column. This method gives five fractions, i.e. aliphatic and monoaromatic hydrocarbons, polycyclic aromatic hydrocarbons, PCBs with two or more ortho-chlorines, mono-ort/io PCBs, and non-ortho PCBs and PCDD/Fs. This method employed five switching valves and was successfully used with extracts of sediments, biological samples and electrostatic filter precipitates. 

Nickel in the presence of ammonia is often used for reduction of nitriles to primary amines. The reaction is done at elevated temperatures and pressures ( 100 C, 1000 psig) unless massive amounts of nickel are used. Cobalt is used similarly but mainly under even more vigorous conditions. Nitriles containing a benzylamine can be reduced over Raney nickel to an amine without hydrogenolysis of the benzyl group (7). A solution of butoxycarbonyl)-3-aminopropyl]-N-<3-cyanopropyl)benzylamine (13.6 g) in 100 ml of ethanol containing 4 g. NaOH was reduced over 3.0 g Raney nickel at 40 psig for 28 h. The yield of A/ -benzyl-Air -(f-butoxycarbonyl)s >ermidine was 95% (7). 

Therapeutic Function Antihypotensive Chemical Name 3-(2-Aminopropyl)phenol Common Name Alpha-methyltyramine... 

Preparation of 3-(N-Formyl-N-Methyl)-Aminopropyl Chloride 50 grams of 3-(N-formyl-N-methyl)-aminopropanol-1 obtained above is dissolved in a mixture of 100 ml of chloroform and 25 grams of pyridine. 40 grams of thionyl chloride is then slowly added while maintaining the temperature below 65°C. After 6 hours of refluxing, the mixture is washed with water, then with sodium bicarbonate solution and again with water and then dried over magnesium sulfate and the solvent distilled off in vacuo. Fractional distillation at 1 mm pressure yields substantially pure 3-(N-formyl-N-methyl)-aminopropyl chloride. 

Preparation of 5-[3-(N-Formyl-N-Methyl)-Aminopropyl]-SH-Dibenzo[a,d] Cycloheptene ... 

To a suspension of 3.9 grams of potassium amide is slowly added a solution of 19.2 grams (0.1 mol) Of 5H-dibenzo[a,d] cycloheptene in 600 ml of ether with stirring. The suspension is refluxed with stirring for 3 hours, then cooled to room temperature and a solution of 0.1 mol of 3-(N-formyl-N-methyl)-aminopropyl chloride in 100 ml of ether added. The mixture is then refluxed with stirring for 5 hours and then 100 ml of water added. The ether layer is then washed with dilute hydrochloric acid, then water and then dried over magnesium sulfate and evaporated to dryness yielding 5-[3-(N-formyl-N-methyl)-amino-propyl] -5H-dibenzo[a,d] cycloheptene. 

Preparation of 5-(3-Methylaminopropyl)-5H-Dibenzo[a,d]Cycloheptene from 5-[3-(N-Formyl-N-Methylj-Aminopropyl]SH-Dibenzo[a/i]Cycloheptene 29.5 grams of 5-[3-(N-formyl-N-methyD-aminoprOpyl] -5H-dibenzo[a,d] cycloheptene is refluxed for 24 hours under nitrogen in a solution of 36.3 grams of potassium hydroxide in 378 ml of n-butanol. After cooling to room temperature, the solvent Is evaporated in vacuo, the residue is stirred with 200 ml of water, 300 ml of n-hexane, the layers separated, the water layer extracted with 100 ml of n-hexane and the combined hexane layers washed with water (2 x 100 ml) and then with... 

The following is an alternative method of preparation 1 gram 2-(7-chloropropyl)-s-tri-azolo-[4,3-al-pyridine-3-one and 5 ml saturated ammonia alcoholic solution are heated for 5 hours in a closed tube at 100°C. The contents of the tube are cooled, the ammonium chloride filtered out and the solvent is removed. There remains a residue of 0.9 grams 2-(7-aminopropyl)-s-triazolo-[4,3-al -pyridine-3-one. 

Starting from a collection of samples remarkably well resolved (alpha > 6) on Chiralcel OD (Cellulose tris(3,5-dimethylphenylcarbamate) coated on aminopropyl silica), a putative three-point enantiophore for binding to CSR was derived (Fig. 4-10). This enantiophore query was used to search (CFS 3D search) within a list comprising 4203 compounds tested on Chiralcel OD. From this search domain of CHIRBASE 3D, 191 structures were found to match the enantiophore. 

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