Synthese von Oxazolidinen durch Einwirkung von Aldehyden auf Hydramine

Abstract

Von den S a l z e n des Dirnethyliithannlamins sind durch die Untersuchungen von M o r l e y ' ) , L a d e n b u r g e ) , K n o r r s ) und F r e n n d ' ) das Chloroplatinat und Chloraurat bekannt geworden. Wir baben zur weiteren Charakterisirung das Pikrat und Pikrnlnnat5) dargestellt.Das P i k r a t ist in Wasser ond Alkohol ziemlich leicht liielich.

The Oxazolidines.

“…Knorr and coworkers (75,76) condensed the reactants in boiling ether in the presence of solid potassium carbonate; they pointed out, however, that some stable compounds, such as those derived from aromatic aldehydes or ketones, form as soon as the reagents are mixed. Indeed, the condensation can be carried out without any catalyst.…”

“…It gives a product which may be 3-carbopropoxyoxazolidine (I), although its discoverers had originally assigned to it the formula (II) of N-carbopropoxy-N-methylaminoacetaldehyde. An The comparative ease with which different aminoalcohols and different car- Ci.......... Ethanolamine (7,8,9,10,11,13,14,18,28,35,75,76,85,87,88,89,108) Cl.......... N-Methylethanolamine (14,IS,19,53,74,75) l-Amino-2-propanoI (34) 2-Amino-l-propanol (58) 1-Amino-2,3-propanediol (20,83) 2-Amino-l, 3-propanediol (100) l-Amino-3-chloro-2-hydroxypropane (22,23,103) C........... Diethanolamine (19,56) jV-Ethvlethanolamine (38,66) 2-Amino-2-methvl-l-propanol (58,105) 2-Amino-l-butanol (8, 58, 88s) 2-Amino-2-methvl-l, 3-propanediol Aminotrimethy lolmethane (1,34,59,106) (1, 91, 92, 106) Ci.......... l-Amino-3-methyl-2-butanol…”

Cyanoethylation of Aromatic Aldehyde Imines Containing a Hydroxy Group in the β- or γ-Position. Synthesis of 3-Cyanoethyl-1,3-oxazacycloalkanes

“…A solution of 3 g (0.02 mol) of N-benzylidene-2-hydroxyethylalmine (Ia) and 2.12 g (0.04 mol) of acrylonitrile (stabilized with hydroquinone) in 10 ml of dry benzene was heated for 8 h. The solvent was distilled off, and the residue was distilled under reduced pressure to isolate 1.9 g of initial Schiff base Іa, bp 104-106°C (2 mm), n D 20 = 1.5690 [9], and 1.1 g (27%) of Va, bp 145°C (2 mm), n D 20 = 1.5350. The IR spectra were obtained on a Specord 75IR instrument from samples dispersed in mineral oil.…”

Consequences of the formation of 3,4-dimethyl-5-phenyl-1,3-oxazolidine on the analysis of ephedrines in urine by gas chromatography and a new method for confirmation as N-trifluoroacetyl-O-t-butyldimethylsilyl ether derivatives

“…The formation of the oxazolidine derivatives as products from condensation between ␤-aminoalcohols and aldehydes [13,14] has already been observed for pseudoephedrine and ephedrine [15,16], and the differences in stereochemistry of the diastereomers are conserved in the oxazolidines [17,18]. The condensation of aldehydes with ␤-hydroxyethylamines takes place with primary [19] and secondary amines [20], while tertiary amines are incapable of undergoing such reaction [20].…”