One of the tricks I learned as a process chemist is to look for someone who has already made your compound (or a close analogue) before approaching it on first principles.
You're in luck, actually. It's not the compound you want exactly, but it's a general recipe using the old classic coupling reagent, dicyclohexyl carbodiimide (DCC), that should be adaptable.
I found this, specifically:
Esterification of cinnamic acids with N-protected amino alcohol[30]. Cinnamic acids(1.5mmol), DCC (1.5 mmol) and DMAP (0.0224mmol) are dissolved in 10mL of dry THF. The reaction mixture is stirred under argon at 0Сand then, after 10 min N-protected amino alcohol (0.6 mmol) is added. The mixture is kept under vigorous stirring and cooling (0С) for 60 min and then is allowed to stand at room temperature overnight. The residue of dicyclohexylcarbamide is filtered and washed with cold ethyl acetate. The combined solutions are evaporated under vacuum and the residueis purified by column chromatography on silica
Your "cinnamic acid" would be the p-coumaric acid, and instead of the amino alcohol, use your 2-phenylethanol. Use the same molarity, recalculate the weights to account for different masses of your starting materials and I think it's workable. (You may not need to purify by column chromatography, depending.) The usual twiddles may be made too, e.g. Ar is not critical, temperature can vary, solvent is not strictly required to be as specified, etc.
However, I hate to spoil your fun, but I suspect that such a compound would only be a good drug when you're measuring it directly against MAO enzymes in a petri dish. For a compound to work as a "drug" and be orally/centrally active or have a half life greater than a minute or two, it needs to have certain properties to allow it to get from your stomach, through the liver, into the blood, past the blood brain barrier, and then to the target enzymes it acts upon. Notably to me, it's not particularly water soluble. I think it will fall under the same class as quercetin, which looks nice in a petri dish, but in real life cannot even make it out of your gut into your blood. Nice opportunity to learn about esterification though?