Were your starting materials pure? HPLC, GC confirmations required. Also, do not use old raw materials as a general guideline for any synthesis. Neutralize the HCl salt at pH 7 (using triethylamine or another preferential base) and recollect the free amine separately. It would be good if you use the free amine separately and not in situ generated free amine. Now run your reaction with the catalyst and have the starting reaction medium slightly acidic. You can also try the neutral reaction medium to run your reaction and  to obtain the product if you succeed in getting substantial yields. This could be a new approach to the synthesis. Report back on the reactions. Will move on the other issues.

I'd add about 0.8 eq of TEA, this should free up enough of the amine to undergo imine formation while still leaving enough of the conjugate acid around to assist in this process.

Mr./Miss./Mrs. Iqbal,

Please pay attention to:

Journal of Materials Science: Materials in Medicine, January 2009, Volume 20, Issue 1, pp 33-44

excess of propylene oxide in MeOH or EtOH works well to free base amino acids from their hydrochloride salts (J. Org. Chem., 44(15), 2732, 1979)

I hope this helps

If you want to isolate tryptamine as a free base from tryptamine.HCl it is better to stir the salt with little more than equimolar sodium carbonate in methanol/acetone for 1-2 hr and then filter the inorganic material . Now you have free base in filtrate and use it for onward reaction.I hope it will work nicely.

Above suggestion is good, I'd suggest equimolar amount of triethylamine to release free tryptamine, then add aldehyde and 3 equivalent of anhydrous MgSO4 as dehydrating agent to drive reaction in forward direction, normalyy in dry DCM under reflux should work.

What is the DCM!?

You can try using Sodium Acetate for this purpose

Dear Tahseen Iqbal

Try neutralize tryptamine hydrochloride with sodium bicarbonate or sodium acetate.

Good luck

 DCM=dichloromethane

Dear Tahseen Iqbal

The answer of Vishnu Ji Ram is also useful.