Reaction of 1,2-dibromoethane with primary amines: Formation of N,N′-disubstituted ethylenediamines RNH-CH2CH2-NHR and homologous polyamines RNH-[CH2CH2NR]n-H

Tetrahedron

Volumn 59, Issue 38, 2003, Pages 7565-7570

  Denk, Michael K ^a   Krause, Mike J ^a   Niyogi, Debyani F ^a   Gill, Nachhattarpal K ^a  

^a UNIVERSITY OF GUELPH   (Canada)

Author keywords

Alkylation; Amines; Chelate ligands; Ethylenediamine; Polyethyleneimine

Indexed keywords

1,2 DIBROMOETHANE; 1,4 DI TERT BUTYLPIPERAZINE; 1,4 DIISOPROPYLPIPERAZINE; 1,4 DIMETHYLPIPERAZINE; 1,4 DIPHENYLPIPERAZINE; 1,4,7 TRI TERT BUTYL 1,4,7 TRIAZAHEPTANE; 1,4,7 TRIETHYL 1,4,7 TRIAZAHEPTANE; 1,4,7 TRIISOPROPYL 1,4,7 TRIAZAHEPTANE; 1,4,7 TRIMETHYL 1,4,7 TRIAZAHEPTANE; 1,4,7 TRIPHENYL 1,4,7 TRIAZAHEPTANE; 1,4,7,10 TETRAETHYL 1,4,7,10 TETRAAZADECANE; 1,4,7,10 TETRAISOPROPYL 1,4,7,10 TETRAAZADECANE; 1,4,7,10 TETRAMETHYL 1,4,7,10 TETRAAZADECANE; 1,4,7,10,13 PENTAISOPROPYL 1,4,7,10,13 PENTAAZATRIDECANE; AMINE; DIAMINE DERIVATIVE; N,N' DI TERT BUTYLETHYLENEDIAMINE; N,N' DIETHYLETHYLENEDIAMINE; N,N' DIETHYLPIPERAZINE; N,N' DIISOPROPYLETHYLENEDIAMINE; N,N' DIMETHYLETHYLENEDIAMINE; N,N' DIPHENYLETHYLENEDIAMINE; PIPERAZINE DERIVATIVE; POLYAMINE DERIVATIVE; POLYETHYLENEIMINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DISTILLATION; ISOLATION PROCEDURE; MASS SPECTROMETRY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SEPARATION TECHNIQUE; SUBSTITUTION REACTION;

EID: 0041829485     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(03)01149-9     Document Type: Article

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56. 3 filtration as described in the Section 3. Commercially available N,N′ -diphenylethylenediamine (Aldrich D2, 700-4N, mp 65-67°C) contains ca. 2% of N,N′-diphenylpiperazine. Previously reported melting points (a) Schönberg A. Chem. Ber. 116:1983;2068-2073. (65-67°C) (b) Schönberg A. Chem. Ber. 117:1984;3388-3399. (64-66°C).
57. 3 filtration as described in the Section 3. Commercially available N,N′ -diphenylethylenediamine (Aldrich D2, 700-4N, mp 65-67°C) contains ca. 2% of N,N′-diphenylpiperazine. Previously reported melting points (a) Schönberg A. Chem. Ber. 116:1983;2068-2073. (65-67°C) (b) Schönberg A. Chem. Ber. 117:1984;3388-3399. (64-66°C).
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62. Quarternary ammonium salts were suggested as other possible side products by one referee. While we have no evidence for their formation under the reaction conditions employed, their formation under more forcing conditions seems indeed likely.