The condensation of 2,3-dihydrobenzodioxin-6-carbaldehyde (I) with 5(S)-phenylmorpholin-2-one (I) in refluxing toluene gives the adduct (III), which is treated first with pyrrolidine (IV) in chloroform and then with HCl in refluxing methanol to yield the pyrrolidide (V). The reduction of (V) with LiAlH4 in THF affords compound (VI), which is treated with H2 over Pd/C in THF/methanol/water to provide the aminoalcohol (VII). Finally, the amino group of (VII) is acylated by means of palmitoyl chloride (VIII) and DIEA in dichloromethane to furnish the target palmitoylamide.
Methenamine is added to a solution of bromide (I) in CHCl3 and after treatment with concentrated HCl, amine (II) is obtained. NaOAc and palmitoyl chloride (III) are added to a solution of (II) in THF to yield derivative (IV) which is finally converted to (V) by treatment with paraformaldehyde and pyrrolidine in ethanol, followed by treatment with concentrated HCl, reduction with NaBH4 and final hydrolysis with diluted HCl.