Scheme 1: The synthesis of PPAP Phenylpropylaminopentane (PPAP)and benzofuranylpropylaminopentane (BPAP)are newly synthesized derivative of the drug selegeline.

These compounds are catecholaminergic activity enhancers which have uses treating parkinsons disease, alzheimers, and depression. They also have the interesting effect of dramatically increasing lifespan in rats. The following is a scheme for the preparation of PPAP Materials Needed: 1-Iodobutane (not in stock, 10$, 25g) Benzaldehyde Lithium aluminum hydride (not in stock, 10g, 25$) Ammonium acetate (not in stock, sigma aldrich, 16$, 50g) Glacial acetic acid Acetic anhydride Sodium nitrite Hydrochloric Acid Dicholoromethane Anyhdrous tetrahydrofuran.

Step 1 is the modified victor reaction of iodobutane to nitrobutane, bypassing an expensive precursor. This can then be separated from the haloalkane and the nitrite ester byproducts by distillation and used in the next step. Step 2 is the henry reaction using ammonium acetate as a catalyst to promote the condensation. The reflux is to drive water off the reaction and drive it forward Pyridine acetate could also be formed from glacial acetic acid and pyridine, which could be used as a catalyst and which might work, though some modification might need to be made. Step 3 is the LiAlH reduction giving the amine. This also should reduce some of the henry reaction side products. to the same amine. workup by destroying the hydride and filtering. Step 4 is the formation of the propylamide wtih acetic anhydride. Step 5 is a final reduction with LiAlH4. The henry reaction is sensitive and reversible, so steps 2 and 3 would need to be completed the same day. The proposed timeline then would be the formation of the nitroalkane and purification on day one, steps 2 and 3 on day 2, and steps 4 and 5 followed by workup on the final day. Since information on

solubility of the compound is scarce it may be necessary to purify by chromatography. If necessary I could come in the next tuesday to do the necessary analysis of the final product if short on time.