6483-50-7Relevant articles and documents
Electroactivated alkylation of amines with alcohols: Via both direct and indirect borrowing hydrogen mechanisms
Appiagyei, Benjamin,Bhatia, Souful,Keeney, Gabriela L.,Dolmetsch, Troy,Jackson, James E.
supporting information, p. 860 - 869 (2020/02/21)
A green, efficient N-alkylation of amines with simple alcohols has been achieved in aqueous solution via an electrochemical version of the so-called "borrowing hydrogen methodology". Catalyzed by Ru on activated carbon cloth (Ru/ACC), the reaction works well with methanol, and with primary and secondary alcohols. Alkylation can be accomplished by either of two different electrocatalytic processes: (1) in an undivided cell, alcohol (present in excess) is oxidized at the Ru/ACC anode; the aldehyde or ketone product condenses with the amine; and the resulting imine is reduced at an ACC cathode, combining with protons released by the oxidation. This process consumes stoichiometric quantities of current. (2) In a membrane-divided cell, the current-activated Ru/ACC cathode effects direct C-H activation of the alcohol; the resulting carbonyl species, either free or still surface-adsorbed, condenses with amine to form imine and is reduced as in (1). These alcohol activation processes can alkylate primary and secondary aliphatic amines, as well as ammonia itself at 25-70 °C and ambient pressure.
PROCESS FOR PREPARING A CYCLIC TERTIARY AMINE
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Page/Page column 8, (2012/04/23)
A process for preparing a cyclic tertiary amine of the formula I where A is a C4-alkylene group, a C5-alkylene group or a —(CH2)2—B—(CH2)2— group, where B is oxygen (O) or an N—R1 radical and R1 is C1-C5-alkyl, aryl or C5-C7-cycloalkyl, and the radical R2 is a linear or branched C2-C16-alkyl, C5-C7-cycloalkyl or C7-C20-aralkyl, in which (i) an amino alcohol II from the group consisting of 1,4-aminobutanol, 1,5-aminopentanol, aminodiglycol (ADG) and aminoethylethanolamine of the formula IIa where R1 is as defined above or hydrogen (H), in which case R1═R2 in the amine I, is reacted with a primary or secondary alcohol R2OH (III) at a temperature in the range from 150 to 270° C. in the liquid phase in the presence of a copper-comprising heterogeneous catalyst in a reactor.
Reaction of 1,2-dibromoethane with primary amines: Formation of N,N′-disubstituted ethylenediamines RNH-CH2CH2-NHR and homologous polyamines RNH-[CH2CH2NR]n-H
Denk, Michael K.,Krause, Mike J.,Niyogi, Debyani F.,Gill, Nachhattarpal K.
, p. 7565 - 7570 (2007/10/03)
The reaction of primary amines RNH2 (R: Me, Et, iPr, tBu and Ph) with 1,2-dibromoethane gave N,N′-disubstituted ethylenediamines R-NH-CH2CH2-NH-R (1) in yields ranging from 10% (1a; R=Me) to 70% (1d, R=tBu; 1e, R=Ph). Pipe
