Phenyl Ethylamine

Cleavage to 2-phenyl-ethylamine, phenyl-acetaldehyde and phenyl-acetic acid N-acetylation... 

On mixing isobutyraldehyde, ethylamine, phenyl isocyanide and benzoic acid, all steps in the above reaction occur in one-pot. Intermediates I-III are not isolated, and the presence of some of them was confirmed by spectroscopy. 

Acetophenone similarly gives an oxime, CHjCCgHjlCtNOH, of m.p. 59° owing to its lower m.p. and its greater solubility in most liquids, it is not as suitable as the phenylhydrazone for characterising the ketone. Its chief use is for the preparation of 1-phenyl-ethylamine, CHjCCgHslCHNHj, which can be readily obtained by the reduction of the oxime or by the Leuckart reaction (p. 223), and which can then be resolved by d-tartaric acid and /-malic acid into optically active forms. The optically active amine is frequently used in turn for the resolution of racemic acids. 

Zincke-type salts derived from other aromatic nitrogen heterocycles also undergo Zincke reactions. The isoquinolinium salt 6 (Scheme 8.4.16) permitted incorporation of a phenyl ethylamine chiral auxiliary, providing salt 48. In this context and others (vide infra), Marazano and co-workers found that refluxing -butanol was a superior solvent system for the Zincke process. Additionally, the stereochemical integrity of the or-chiral amino fragment was reliably maintained. 

To understand the unpredictable nature of the Pictet-Gams reaction, Hartwig and Whaley conducted the first mechanistic studies in 1949. Their work focused on substituent effects when directly attached to the ethylamine side chain. They also investigated a variety of dehydration agents in order to identify optimal reaction conditions. It was determined that formation of the isoquinoline structure was virtually impossible when alkyl or phenyl substituents were placed in the 4-position of the ethylamine side chain. 

A mixture consisting of 4 grams of 1,2,3,4-tetrahydro-4,4-dimethyl-7-methoxy-isochromane-dione-(1,3) (MP 95° to 97°C), 2.53 grams of 4-aminosulfonyl-phenyl-(2)-ethylamine and 150 ml of xylene was heated for 2 hours at its boiling point in an apparatus provided with a water separator. Thereafter, the reaction mixture was allowed to cool and was then vacuum-filtered, and the filter cake was recrystallized from n-propanoi in the presence of activated charcoal. 2.9 grams (58% of theory) of 1,2,3,4-tetrahydro-4,4-dimethyl-2-(p-amino-sulfonylphenyl-(2)-ethyl]-7-methoxy-isoquinolinedione-(1,3), MP 203° to 205°C, of the formula below were obtained. 

D) 4 -[N-Ethyi-1 "-Methyl-2 -(4" -Methoxyphenyl)Ethylamino]Butyi-3,4-Dimethoxybenzoate Hydrochloride 10.3 g of 4 -iodobutyl-3,4-dimethoxybenzoate and 11.0 g of N-ethyl-p-methoxyphenylisopropylamine (obtained by catalytic reduction of an alcoholic solution of an excess quantity (60%) of p-methoxy-phenyl-acetone, to which was added a 33% (weight-for-weight) aqueous solution of ethylamine, with Pt as a catalyst), were boiled in 200 ml of methyl ethyl ketone for 20 hours, cooled and the iodine ion was determined the reaction was found to be complete. Then the methyl ethyl ketone was evaporated in vacuo and the residue was dissolved in 300 ml of water and 30 ml of ether the layers were separated and the water layer was extracted twice more with 20 ml portions of ether. 

What stereoisomers would result from reaction of (z )-laclic acid with (S)-l-phenyl-ethylamine, and what is the relationship between them ... 

The P. notatum took up the P-phenyl ethylamine, converted it to p-phenylacetate, which was subsequently attached to the 6-amino group of penirillanic add to give benzyl penicillin (penidllin G). We can represent this process by ... 

The stereochemistry of the addition of amines to acetylenic sulfones has been investigated by Truce and coworkers74. Reaction of phenyl 1-propynyl sulfone with ethylamine gives a mixture of ( )- and (Z)-isomeric adducts (equation 90)75. 

Phenyl N-acetylcarbazate 1529 cyclizes on boiling with excess TCS 14/tri-ethylamine in toluene to give 5-methyl-l,3,4-oxadiazohne-2-one 1530 in 65-70% yield [41, 59, 60]. The same type of cyclization was subsequently described for re-... 

When 5ym.-ethylphenylurea is heated alone at 160°, ethylamine escapes and the phenylisocyanate and aniline combine to form 5ym.-diphenylurea. The imea dearrangement then provides the true explanation of the apparently metathetical reaction in which the ethyl groups of 5ym.-diethylurea are successively replaced by phenyl. ... 

Figure 4.40 Dependence of yield on specific interfacial area between aqueous or organic phase. The four combinations AC-BD refer to the respective reactions between dl-1-phenyl-ethylamine (A), 4-amino-l-benzylpiperidine (B), 3-nitrobenzoyl chloride (C), and 3,5-dinitrobenzoyl chloride (D) [23],...

The formation of such complexes apparently involves a delicate balance of binding forces, since a-phenyl-ethylamine 30 shows only modest tendencies to form 2 1 complexes and its stacking efficiency is reduced. The structural details of these complexes are not known, but intermoleeular NOE experiments favor structures such as shown in 31. The distance between the aromatic and amine recognition sites in the... 

Fig. 1. Changes in the chemical shift of protons lining the cleft of 13 (H4) H,) as P-phenyl-ethylamine is added...

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