Amination of a glyoxalyl chloride; (tris-indoleglyoxalyl)amine

Christine R. Whitlock ([email protected]),
A contribution from the Whitlock Group, Georgia Southern University

Chemicals Used
indole (Aldrich) diethyl ether (Fisher) oxalyl chloride (Aldrich) tris(2-aminoethyl)amine (Aldrich) triethylamine (Aldrich) THF (Aldrich) methanol (Fisher)

Procedure
To indole (10.07 g, 86.1 mmol) in ether (200 mL) was added dropwise oxalyl choride (14.6 g, 114.6 mmol) over 15 mins. After stirring for 30 min, the solution was filtered to yield indole-3-glyoxalyl chloride as a yellow solid, which was rapidly dissolved in THF (50 mL). To the indole-3-glyoxalyl chloride in THF at 0°C was added a solution of tris(2-aminoethyl)amine (6.14 g, 42.0 mmol) and triethylamine (42.3 mmol) in THF (10 mL). After stirring at 0°C for 1 h, the solution was filtered and the filtrate was evaporated to yield tris(2-[indole-3-glyoxylamido]ethyl)amine as a beige solid, which was recrystallized in MeOH to yield glassy crystals.

Author's Comments
The reaction is an efficient way to prepare tris(2-[indole-3-glyoxylamido]ethyl)amine. The glyoxalyl choride intermediate is unstable, thus cold temperatures are necessary. Could be reliable with other acyl chlorides.

Data
Yield 5.93 g (31.4%); mp > 250°C. ¹H NMR (250 MHz, DMSO-d₆) _8.75 (s, 3H), 8.65 (t, J=5.29 Hz, 3H), 8.14 (d, J=6.9 Hz, 3H), 7.47 (d, J=7.1 Hz, 3H), 7.22 (t, J=7.0 Hz, 3H), 7.16 (t, J=7.0 Hz, 3H), 3.31 (m, 6H, Ha), 2.71 (bt, 6H, Hb); MS (M+1)⁺ = 660 for C₃₆H₃₃N₇O₆

Lead Reference
Carpenter, R. A.; Farley, A. R.; Cox, J. R.; Dobson, A. J.; Whitlock, C. R. J. Undergrad. Chem. Res. 2004, 1, 114.

Other References

This page has been viewed approximately 2894 times since records began.

Get CDX file

SyntheticPages^TM are for use exclusively by those with training and experience in synthetic chemistry. While contributors are asked to identify hazards and to use methods designed to reduce risk, no formal hazard or risk assessments are included, and these procedures must be conducted at one's own risk. SyntheticPages, its editors, owners and associates do not warrant or guarantee the safety of individuals using these procedures and hereby disclaim any liability for any injuries or damages claimed to have resulted from or related in any way to the procedures herein. Copyright ©2005 Synthetic Pages

Comment on this page!