In this reductive methylation method formic acid serves as a reductunt;
anyone else trying it with tryptamine?
See:
[1] Moore, M.L. Org. React., 1949, 5, 301
[2] J.C.S., 1342 (1950)
[3] J. Org. Chem., 50, 1110 (1985)
[4] J. Org. Chem., 51, 5169 (1986)
[5] Joseph Casanova and Praveena Devi, Synth. Comm., 23(2), 245-251 (1993)
Procedure below is taken from ref. [5]:
5 mmol of prime amine is dissolved in minimal amount of ether and placed in a 3-neck rbf equipped with a reflux condenser and a magnetic stirrer.
Solution is cooled to 0 C followed by addition of formaldehyde (38%, 9 mL) and formic acid ( 85%, 10 mL)
(Authors in [5] report that reaction is exotermic upon addition of formic acid,
in the case tryptamine it was not that obvious to me.)
After the addition the mix is heated at 80 C for 10 hrs
Cooled to RT
Ether was added (50 mL), mix was neutralized with 20% NaOH and stirred for 10 min.
Extracted with ether, -combined organic layers were dried over MgSO4. and the solvents removed.
------------
DO IT NOW!
Z_Hound
Any Possession is a Demonic Possession!