Lithium n-propylamine

P. E. Koenig, J. M. Morris, E. 3. Blanchard, and P. S. Mason, 3. Org.,76,4111 (1961) Lithium-n-Propylamine. Leonard et al. have used this reducing combination to prepare enamines which are stable to hydrolysis because the functional group is contained in abi- or tricyclic system. Examples ... 

Li. ri Propylimlne, NHiCH CHiNHd Lithium, n-Propylamine, Ethvlenediamine 7439-93-2/107-10-8 107-1S-3 5 5 5.0 Flammable. 

Lithium n-propylamine Partial and total hydrogenation of carbazoles... 

To a dry flask containing 415 ml of n-propylamine and 10.15 gm (1.45 gm-atoms) of chopped lithium wire segments is added, with stirring, 21.3 gm (0.125 mole) of l-methyl-l,2,3,4-tetrahydroquinoline, and the mixture is stirred for 16J hr under a nitrogen atmosphere. The un reacted lithium is removed, the excess n-propylamine is distilled from the flask, the semisolid residue is cooled in an ice bath, overlaid with ether, and then neutralized slowly with solid ammonium chloride. The mixture is cautiously diluted with water, the ether layer separated, the water layer extracted with ether, the ether layers combined, dried, concentrated, and the residue is distilled to alford 19.8 gm... 

Ruff et al. in a series of publications described the synthesis of amine complexes of aluminum hydride [32, 33]. Their study investigated the reaction of these materials with typical Lewis bases in order to define the conditions for the stability of aluminum hydride derivatives in which the aluminum atom exhibits a coordination number of five. They first described methods for making tertiary alkyl amine complexes of aluminum hydride utilizing lithium aluminum hydride and an amine hydrochloride. A finely ground lithium aluminum hydride was placed together with trimethylammonium chloride (ratio 1 2). They prepared other trialkylamine alanes and the N-dialkylaminoalanes, in a similar fashion. These adducts of alane were found to sublime readily at temperatures up to 40 °C except for the tri-n-propylamine alane, which sublimed very slowly and could also be recrystallized from hexane at — 80 °C. 

Amides are more conveniently reduced with lithium aluminum hydride in ether solution to yield amines with the same carbon content, e.g, tri-ethylamine from N,N-diethylacetamide (50%) and ethyl-n-propylamine from N-ethylpropionamide (53%). ° The same conversion has been accomplished by an electrolytic reduction. ... 

Treatment of oc-cyclopropyl ketones with lithium in a mixture of N,N-d2 propylamine and hexamethylphosphortriamide is a recently reported method for deuterium labeling via reductive ring opening. This reaction provides y-labeled ketones in good yield (70-100%) and isotopic purity (85-93%). 

Unsymmetrical secondary amines are readily prepared in good yields by the catalytic reduction of Schiff bases at moderate temperatures in high-or low-pressure equipment. Many examples have been cited. The intermediate imines are prepared from primary amines and aldehydes—very seldom from ketones—and may be used without isolation (cf. method 431). For the preparation of aliphatic amines, e.g., ethyl-w-propylamine and n-butylisoamylamine, a prereduced platinum oxide catalyst is preferred with alcohol as the solvent. Schiff bases from the condensation of aromatic aldehydes with either aromatic or aliphatic amines are more readily prepared and are reduced over a nickel catalyst. In this manner, a large number of N-alkylbenzylamines having halo, hydroxyl, or methoxyl groups on the nucleus have been made. Reductions by means of sodium and alcohol and lithium aluminum hydride have also been described,... 

A round-bottom flask, with a side arm fitted with an argon balloon, is charged with n-butyl chloride (46.3 g, 0.5 mol), di-/-propylamine (freshly distilled on CaH2, 50.6 g, 0.5 mol), and dry THF (250 mL). Lithium (wire cut into pieces, 7 g, 1 mol) is added portionwise via the side arm under sonication. 

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