2-Aminoethyl

Monoethanolainine, 2-aminoethyl alcohol, 2-hydroxyelhy amine, HOCH2CH2NH2. M.p. 10-5°Q b.p. 17UC. 

Diethyl carbinol (7) Stearyl alcohol (12) Butyl cellosolve (17) 2 Aminoethyl alcohol ... 

Supplement 1942 195-449 Hydroxy-amines Aminoethyl alcohol, 274. Carbonyl-amines Aminoacetaldehyde, 307. Aminoacetone, 314. Hydroxy-carbonyl amines Glucosamine, 328. Aminocarboxylic acids Glycine, 333. Hydroxylamines, 534. Hydrazines, 546. Azo Compounds. 562. Oryano-metallic Compounds, 580. 

An intramolecular version offers useful synthetic methods for heterocycles. The total syntheses of a- and 7-lycoranes (373 and 374) have been carried out by applying the intramolecular aminochlorination of the carbamate of 5-(2-aminoethyl)-l,3-cyclohexadiene (372) as a key reaction[312,313]. Interestingly, the 4,6- and 5,7-diene amides 375 and 377 undergo the intramolecular amina-tion twice via x-allylpalladium to form alkaloid skeletons ofpyrrolizidine (376) and indolizidine (378), showing that amide group is reactive[314]. 

Chapters 9, 10 and 11 describe methods for substitution directly on the ring with successive attention to Nl, C2 and C3. Chapters 12 and 13 are devoted to substituent modification as C3. Chapter 12 is a general discussion of these methods, while Chapter 13 covers the important special cases of the synthesis of 2-aminoethyl (tryptaminc) and 2-aminopropanoic acid (tryptophan) side-chains. Chapter 14 deals with methods for effecting carbo cyclic substitution. Chapter 15 describes synthetically important oxidation and reduction reactions which are characteristic of indoles. Chapter 16 illustrates methods for elaboration of indoles via cycloaddition reactions. 

One of the virtues of the Fischer indole synthesis is that it can frequently be used to prepare indoles having functionalized substituents. This versatility extends beyond the range of very stable substituents such as alkoxy and halogens and includes esters, amides and hydroxy substituents. Table 7.3 gives some examples. These include cases of introduction of 3-acetic acid, 3-acetamide, 3-(2-aminoethyl)- and 3-(2-hydroxyethyl)- side-chains, all of which are of special importance in the preparation of biologically active indole derivatives. Entry 11 is an efficient synthesis of the non-steroidal anti-inflammatory drug indomethacin. A noteworthy feature of the reaction is the... 

Starting from 2-bromoethylamine hydrobromide and selenourea, Chu and Mautner (60) prepared the salt of 2-(aminoethyl)-selenopseudourea, which cyclizes upon heating in aqueous solution to give 2-aminoselenazoline (Scheme 58). 

Hydrolysis and subsequent oxidation by air of benzoylated selenazolidines gives N.N -diben20vlbis(2-aminoethyl)diselenide (Scheme 73)... 

ALKANOLAMNES - ALKANOLAMINES FROM OLEFIN OXIDES AND AL ONIA] (Vol 2) (3-(2-Aminoethyl)aminopropyl)trimethoxy silane... 

APHTHALENEDERIVATIVES] (Voll6) (+)-(R,S)-a-(l-Aminoethyl)ben2ene-methanol hydrochloride [154-41-6]... 

Reaction with Sulfur Nucleophiles, Because sulfai is highly nucleophilic, reactions of aziridines with sulfur nucleophiles generally proceed rapidly (111) and with good yields. The reaction of hydrogen sulfide [7783-06S-J with ethyleneimine yields cysteamine [60-23-1] (2-mercaptoethylamine) or bis(2-aminoethyl)sulfide [871-76-1] (2,112) depending on the molar ratio of the reactants. The use of NaHS for the synthesis of cysteamine has also been described (113). 

The reaction of thioethers with ethyleneimine in the presence of acid yields sulfonium compounds. The reaction is reversible under alkaline conditions (125). Compounds in which double-bonded sulfur can exist in tautomerism with a form having a free SH group, such as thiourea (126,127), thiocarboxyhc acids (128), and thiophosphates (129), react to give aminoaLkylated products. The P-aminoethyl thiocarboxylate rearranges to give the amide. 

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