Nice idea. The last reaction can be accomplished with LiAlH4. But there might be a few problems:
- The first compound is not a ketone, it's an amide (or better: an anilide), so the first reaction might not work as expected.
- The second compound is not an enamine and will probably not react like one, it's an amino substituted aromatic ring similar to aniline.
- The product of the alkylation reaction will probably aromatize immediately, leaving you with a 2-pyrrolidyl-tryptamine.