Benzyl-t-butylamine

To a solution of 32 g of benzyl-t-butylamine in 300 ml of absolute ethanol at reflux temperature was added 32 g of 3,5-dibenzyloxy-C0bromoacetophenone in 10 ml of dry benzene. The mixture was refluxed for 20 hours and then evaporated. When absolute ether was added to the residue, benzyl-t-butylamine hydrobromide was precipitated. The precipitated compound was filtered off and to the filtrate was added an excess of 2N sulfuric acid. This caused precipitation of the hydrogen sulfate of 3.5-dibenzyloxy-60-(benzyI-t-butylamino)-acetophenone which was recrystallized from acetone/ether. If the product is crystallized from different organic solvents, the melting point will vary with the type and amou nt of solvent of crystallization, but the product can be used directly for hydrogenation. 

To a solution of 5.6 g of the bromoacetophenone obtained in step lb in 75 ml of acetone was added a solution of 4.9 g of N-benzyl-t-butylamine in 30 ml of acetone. The mixture was refluxed under stirring for 18 hrs, filtered, and evaporated in vacuum. The residue was dissolved in diethyl ether, petroleum ether b.p. 61°-70°C was added, and the yellow precipitate formed filtered off. After washing with water followed by a 1 1 mixture of isopropylalcohol-petroleum ether white crystals were obtained. The identity of the product was confirmed with NMR. Yield 4.6 g. 

N-Benzyl-N-t-butylamine CAS 3378-72-1 EINECS/ELINCS 222-179-6 Synonyms Benzenemethanamine, N-(1,1-dimethylethyl)- Benzyl-t-butylamine N-(t-Butyl) benzylamine Classification Aromatic amine Empirical CnHiyN Formula C6HsCH2NHC(CH3)3 Properties Colorless clear liq. insol. in water m.w. 163.27 dens. 0.881 b.p. 80 C (5 mm) flash pt. 80 C ref. index 1.4970... 

Benzyl-t-butylamine. See N-Benzyl-N-t-butylamine Benzyl butyl ether CAS 588-67-0... 

To a stirred solution of 5.7 g (0.02 m) of 4-benzyloxy-2-ureidoacetophenone in 100 ml of chloroform is added 3.2 g (0.02 m) of bromine. The mixture is stirred at room temperature for about 45 minutes and the solution is concentrated in vacuo at 25°-30°C. The amorphous residue (hydrobromide selt of 4-benzyloxy-a-bromo-3-ureidoacetophenone) is dissolved in 80 ml of acetonitrile and 98 g (0.06 m) of N-benzyl-N-t-butylamine is added. The mixture is stirred and refluxed for 1.5 hours, then it is cooled toOt in an ice bath. Crystalline N-benzyl-N-t-butylamine hydrobromide is filtered. The filtrate is acidified with ethereal hydrogen chloride. The semicrystalline product is filtered after diluting the mixture with a large excess of ether. Trituration of the product with 60 ml of cold ethanol gives 4-banzyloxy-Of-( N-benzyl-N-t-butylamino)-3-ureidoacetophenone hydrochloride, MP 200°-221°C (decomposition). 

The last reaction perhaps involves an intermediate such as 33a which expells a proton and dimethyl sulfide. Formation of the Schiff s base with t-butylamine, reduction with sodium borohydride and hydrogenolysis of the benzyl ether produces sulfonterol (28). Despite the fact that the methylene hydrogen of sulfonterol must be much less acidic than of the corresponding urea proton on carbuterol or the sulfonamide proton on soterenol, good bioactivity is retained. 

BBA. See N-Benzyl-N-t-butylamine p-t-BBA. See 4-t-Butylbenzoic acid BBAB. See 1,4-Bis (bromoacetoxy)-2-butene BBDT. See 4-t-Butyl-1,2-benzenedithiol BBOT. See 2,2 -(2,5-Thiophenediyl) bis [5-t-butylbenzoxazole]... 

Anthracene Anthranilic acid Anthraquinone Antimony pentachloride Benzaldehyde Benzidine dihydrochloride 2,2 -Benzidinedisulfonic acid Benzoguanamine Benzotrifluoride Benzoyl chloride N-Benzylamine N-Benzyl-N-ethyl-m-toluidine Bisphenol A Bromine 4-Bromochloro benzene Butyl acetoacetate n-Butylamine t-Butylamine Ceteareth-15 o-Chloroaniline p-Chloroaniline m-Chlorobenzoic acid o-Chlorobenzoic acid p-Chlorobenzoic acid m-Chlorobenzotrifluoride o-Chlorobenzotrifluoride p-Chlorobenzotrifluoride Chloroform 4-Chloro-2-nitroaniline 2-Chloronitrobenzene... 

D-Aspartic acid Benzophenone-1 N-Benzyl-N-t-butylamine N-Benzylisopropylamine Butyl benzyl phthaiate... 

N-Benzyl-N-t-butylamine 3380-34-5 Irgaquard B 1000 Irgasan DP300 Triclosan Vikol THP Viv-20 3383-96-8... 

The successful preparation of structural analogues of raised the hope that the chemistry of ammoxidation might also be reproduced in solution under mild laboratory conditions suitable for mechanistic studies. Thus we turned our attention to the critical C-N bond formation step to find out whether one can indeed produce ammoxidized product from a radical with a d imido metal center. For our studies diimido complexes (t-B iN)2M(OSiMe3)2 (M = Cr, Mo) [8,9] were selected as models for the postulated active sites in ammoxidation. Benzyl rather than allyl radicals were chosen for study since the products of allyl radical oxidation are not expected to be stable under our reaction conditions and because benzyl and allyl exhibit similar behavior in oxidation reactions [14]. Indeed, when a solution of (t-BuN)2M(OSiMe3)2 in toluene was heated at 100 C in the presence of benzoyl peroxide as a radical initiator, benzylidene-t-butylamine was obtained in up to 52% yield (Table I). The remaining organic products were C02> bibenzyl, and the expected isomeric distribution of (ortho meta para = 63 21 16) of methylbiphenyls. 

Behenalkonium chloride Behenamide N-Benzyldimethylamine Benzyl sulfide Bis-hexamethylenetriamine Butyl acid phosphate n-Butylamine 4-t-Butylbenzoic acid t-Butyl chromate Calcium acetate... 

Aminoethylpiperazine Amyl lactate t-Amyl methyl ether Anisole Benzotrifluoride Benzyl ether Bis (2-chloroethoxy) methane Bromine 1,4-Butanediol Butoxyethyl stearate 3-Butoxy-1,2-propanediol t-Butyl acetate n-Butylamine s-Butylamine Butyl butyrate Butylcyclohexane s-Butylcyclohexane t-Butylcyclohexane Butylcyclopentane s-Butylcyclopentane... 

Thiobis (4-t-octylphenolato)-n-butylamine nickel Uvasorb Nl 14529-40-9 Ceteth-10 14536-17-5 Ferrous ascorbate 14548-46-0 4-Benzoy I py ri d i ne 14548-60-8 Akyposept B Benzyl hem if orm al Preventol D 2... 

A mixture of phenylacetic acid, benzyl alcohol, and tri-n-butylamine in methylene chloride added under argon to a mixture of l-methyl-2-bromopyridinium iodide and methylene chloride, and refluxed 3 hrs. benzyl phenylacetate. Y 97%. F. e., also with l-methyl-2-chloropyridinium iodide, s. T. Mukaiyama et al., Chem. Lett. 1975, 1045 Bull. Chem. Soc. Japan 50, 1863 (1977) carboxylic acid amides from amines (cf. Synth. Meth. 26, 367) s. ibid. 1975, 1163 3,4-dihydro-2H-pyrido-[1,2-a]pyrimid-2-one as acid scavenger cf. ibid. 1976, 13, 57 lactones from hydroxycarboxylic acids (cf. Synth. Meth. 17, 320) with 2-chloropyridine methio-dide and triethylamine s. ibid. 1976, 49 esters with 2 halogeno-3-ethylbenzothia-zolium salts of ibid. 1976, 267 2-chloro-N-methylbenzothiazolium triflate as condensing agent s. F. Souto-Bachiller, G. S. Bates, and S. Masamune, Chem. Com-mun. 1976, 719. 

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