New synthetic route for selectively substituted 1,n-diamines. Synthesis of N-aryl tetra- and pentamethylenediamines

Tetrahedron Letters

Volumn 51, Issue 38, 2010, Pages 5000-5002

  Ramirez, María A ^a   Corona, María V ^a   Blanco, Maria M ^a   Perillo, Isabel A ^a   Porcal, Williams ^b   Salerno, Alejandra ^a  

^a UNIVERSIDAD DE BUENOS AIRES   (Argentina)

^b UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

DIAMINE; N ARYLPENTAMETHYLENEDIAMINE DERIVATIVE; N ARYLTETRAMETHYLENEDIAMINE DERIVATIVE; PIPERIDINE; PYRROLIDINE DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;

AMINATION; AMINOLYSIS; ARTICLE; CHEMICAL REACTION; DRUG SYNTHESIS; HEATING; HYDROLYSIS; MICROWAVE IRRADIATION; TEMPERATURE;

TETRA;

EID: 78549246723     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.07.075     Document Type: Article

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34. General procedure for synthesis of compounds 2: A mixture of the appropriate N- (ω-chloroalkyl)benzamide 3 (0.02 mol) and the corresponding arylamine (0.04 mol) was heated for 1 h under reflux in an oil bath at 120 °C. After cooling, the crude material was treated with hot water (10 mL) in order to extract the arylamine hydrochloride, and then heated for 5 minutes with 10% HCl (10 mL) and filtered before cooling. The filtrate was alkalinized with 10% NaOH to pH 14. The product was filtered, dried, and recrystallized from cyclohexane.
35. 4 (15 mL) was heated at reflux for 7-13 h and monitored by TLC. When the reaction was completed, the solution was made alkaline with 50% aqueous NaOH in an ice bath and extracted with methylene chloride (3 × 5 mL). The organic layers were pooled, washed with water, dried, and evaporated in vacuo affording the corresponding compounds 1 as oils which were purified by column chromatography (chloroform/methanol 8:2 to 1:1).