GABRIEL Amine synthesis


GABRIEL Amine Synthesis Synthesis ol primary amines from alkyl halides  [c.139]

Gabriel Amine Synthesis.206  [c.199]

Gabriel Amine Synthesis  [c.206]

Primaty amines may be prepared from alkyl halides using phthalimide. This is called the Gabriel amine synthesis.  [c.206]

Next the product is acylated with bromoacetyl chloride and the glycine equivalent is constructed in place by a Gabriel amine synthesis (phthalamide anion followed by hydrazine) subsequent to which cyclization to benzodiazepine occurs. The synthesis of the tranquilizer quazepam (88) is finished by thioamide conversion with phosphorus pentasulfide.  [c.197]

Chapter IV. a-Chloromethylnaphthalene (IV,23) benzylamine (Gabriel synthesis) (IV,39) i r.N -dialkylanilines (from amines and trialkyl orthophosphates) (IV,42) a-naphthaldehyde (Sommelet reaction) (IV,120) a-phenyl-cinnamic acid (Perkin reaction using triethylamine) (IV,124) p-nitrostyrene (IV,129) p-bromonaphthalene and p naphthoic acid (from 2 naphthylamine-1 -sulphonic acid) (IV,62 and IV,164) diphenic acid (from phenanthrene) (IV,165).  [c.1191]

A method that achieves the same end result as that desired by alkylation of ammonia but which avoids the formation of secondary and tertiary amines as byproducts is the Gabriel synthesis Alkyl halides are converted to primary alkylamines without contam mation by secondary or tertiary amines The key reagent is the potassium salt of phthal imide prepared by the reaction  [c.929]

The modified procedure involves refluxing the N-substituted phthaUmide in alcohol with an equivalent quantity of hydrazine hydrate, followed by removal of the alcohol and heating the residue with hydrochloric acid on a steam bath the phthalyl hydtazide produced is filtered off, leaving the amine hydrochloride in solution. The Gabriel synthesis has been employed in the preparation of a wide variety of amino compounds, including aliphatic amines and amino acids it provides an unequivocal synthesis of a pure primary amine.  [c.560]

Among compounds other than simple alkyl halides a halo ketones and a halo esters have been employed as substrates m the Gabriel synthesis Alkyl p toluenesul fonate esters have also been used Because phthalimide can undergo only a single alkyl ation the formation of secondary and tertiary amines does not occur and the Gabriel synthesis is a valuable procedure for the laboratory preparation of primary amines  [c.930]

Isobutylamine and 2 phenylethylamine can be prepared by the Gabriel synthesis ten butyl amine N methylbenzylamine and aniline cannot  [c.1245]

Two common rnethods of aziridine synthesis, namely the Wenker method (through -amino alcohols) and the Neber rearrangement (through oxime tosylates) are inapplicable to the synthesis of fused steroidal aziridines. Only the Gabriel synthesis, i.e., ring closure of -halo amines, has been successfully adapted to the steroid system. The recent discovery of additions to olefins of pseudohalogen reagents such as iodine isocyanate, iodine azide, chlorine azide and bromine azide has provided a source of -halo amines which are otherwise difficult to obtain. Trans-halo amines undergo ring closure to aziridines, whereas the cw-isomers eliminate HX on treatment with base to give ketones or other products. A useful complement to pseudohalogen adducts is provided by j8-mesyIoxy azides, obtained by azide ion opening of epoxides followed by mesylation. Another general method of aziridine synthesis, namely nitrene addition to double bonds, has seen only limited application to date due to lack of selectivity of the nitrene reagent, which gives C—H insertion products as well as addition products.  [c.22]

Among compounds other than simple alkyl halides, a-halo ketones and a-halo esters have been employed as substrates in the Gabriel synthesis. Alkyl p-toluenesul-fonate esters have also been used. Because phthalimide can undergo only a single alkylation, the formation of secondary and tertiary anines does not occur, and the Gabriel synthesis is a valuable procedure for the laboratory preparation of primary amines.  [c.930]

Isobutylamine and 2-phenylethylamine can be prepared by the Gabriel synthesis tert-butyl-amine, A-methylbenzylamine, and aniline cannot.  [c.1245]

Reaction of alkyl halides 1 with hexamethylenetetramine 2 (trivial name urotropine) followed by a hydrolysis step, leads to formation of primary amines 3 free of higher substituted amines. This method is called the Delepine reaction, a comparable method is the Gabriel synthesis.  [c.83]

The hydrazinolysis is usually conducted in refluxing ethanol, and is a fast process in many cases. Functional groups, that would be affected under hydrolytic conditions, may be stable under hydrazinolysis conditions. The primary amine is often obtained in high yield. The Gabriel synthesis is for example recommended for the synthesis of isotopically labeled amines and amino acids. a-Amino acids 9 can be prepared by the Gabriel route, if a halomalonic ester—e.g. diethyl bromomalonate 7—is employed as the starting material instead of the alkyl halide  [c.132]


See pages that mention the term GABRIEL Amine synthesis : [c.930]    [c.81]    [c.81]    [c.929]    [c.930]   
See chapters in:

The molecular modeling workbook for organic chemistry  -> GABRIEL Amine synthesis


Organic syntheses based on name reactions and unnamed reactions (1994) -- [ c.139 ]

The molecular modeling workbook for organic chemistry (1998) -- [ c.7 , c.14 ]