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Natural Science Forum / Chemistry / Organic Synthesis / March 2005metylating an amine group.
How would I go about methylating an amine group? It doesn't need to be extremely practical, just work in theory. For example if I have isopropylamine and I want to convert it to isopropylmethylamine what would be a general way of doing it? Mechanisms or named reactions are appreciated. Thank you.  SignatureNeil Lawrence Take out the dog before replying. or reply to group Google search on secondary amine alkylation gives many examples. One of them is: http://www.chem.ucalgary.ca/courses/351/Carey5th/Ch22/ch22-3-1.html Signature--------------------------------------------------------------------- "Are you still wasting your time with spam?... There is a solution!" Protected by GIANT Company's Spam Inspector The most powerful anti-spam software available. http://mail.spaminspector.com > How would I go about methylating an amine group? It doesn't need to be > extremely practical, just work in theory. For example if I have [quoted text clipped - 3 lines] > > Thank you. > How would I go about methylating an amine group? It doesn't need to be > extremely practical, just work in theory. For example if I have [quoted text clipped - 3 lines] > > Thank you. Alkyl bromides will react with amines, ideally in the presence of a base (so try methyl bromide + carbonate in a suitable solvent - I'd try acetone off of the top of my head), but you need to ensure you don't add more than one methyl - if not careful, you might end up by adding 3 and get the quaternary salt. Signature-- Ron Jones >How would I go about methylating an amine group? It doesn't need to be >extremely practical, just work in theory. For example if I have [quoted text clipped - 3 lines] > >Thank you. Borch. Reductive amination. Steve Turner Neil Lawrence schrieb: > How would I go about methylating an amine group? It doesn't need to be > extremely practical, just work in theory. For example if I have [quoted text clipped - 3 lines] > > Thank you. SN2 MeI You could use (MeI or dimethylsulfate/DMF/DIPEA/rt). Reaction mechanism is SN2. Regards > How would I go about methylating an amine group? It doesn't need to be > extremely practical, just work in theory. For example if I have > isopropylamine and I want to convert it to isopropylmethylamine what > would be a general way of doing it? Mechanisms or named reactions are > appreciated. > [quoted text clipped - 4 lines] > > Take out the dog before replying. or reply to group You could use: CH3I or dimethylsulfate in DMF with a non-nucleaophile base, e.g DIPEA (diisopropylethylamine) at room temperature. Mechanism of reaction is SN2. Regards > How would I go about methylating an amine group? It doesn't need to be > extremely practical, just work in theory. For example if I have > isopropylamine and I want to convert it to isopropylmethylamine what > would be a general way of doing it? Mechanisms or named reactions are > appreciated. Ok I found an answer to my own problem and thought others might enjoy it. An amine group is a nucleophile and therefore can participate in Sn1 and Sn2 reactions therefore by reacting my molecule with methylbromide it would add on. Neil > How would I go about methylating an amine group? It doesn't need to be > extremely practical, just work in theory. For example if I have > isopropylamine and I want to convert it to isopropylmethylamine what > would be a general way of doing it? Mechanisms or named reactions are > appreciated. Apart from hitherto proposed methyl halides you may try the Eschweiler-Clarke reaction (HCOH + HCOOH). Michal SignatureMichal Sobkowski Institute of Bioorganic Chemistry, Poznan, Poland http://www.man.poznan.pl/~msob/INDEX2.html |
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