The alkylation of (R)-2-amino-8-methoxy-1,2,3,4-tetrahydronaphthalene (I) with benzyl bromide provided the corresponding dibenzyl amine (II). After conversion of (II) to the hydrochloride salt, methyl ether cleavage by means of BBr3 at low temperature gave rise to naphthol (III). Condensation of (III) with 2-bromoisobutyramide (IV) yielded the naphthyloxybutyramide (V), which was rearranged at 130 C in the presence of NaH to the N-naphthyl-2-hydroxybutyramide (VI). Acid hydrolysis of the amide function of (VI) gave diamine (VII). This was condensed with N-methyl iminodiacetic acid (VIII) using CDI in boiling THF to produce the piperazinedione (IX). After reduction of (IX) to the corresponding piperazine (X) with LiAlH4, the N-benzyl groups were cleaved by hydrogenolysis over Pd/C to afford the primary amine (XI). Finally, coupling of (XI) with 4-mo-pholinobenzoic (XII) acid using CDI provided the title amide.

The alkylation of (R)-2-amino-8-methoxy-1,2,3,4-tetrahydronaphthalene (I) with benzyl bromide provided the corresponding dibenzyl amine (II). After conversion of (II) to the hydrochloride salt, methyl ether cleavage by means of BBr3 at low temperature gave rise to naphthol (III). Condensation of (III) with 2-bromoisobutyramide (IV) yielded the naphthyloxybutyramide (V), which was rearranged at 130 C in the presence of NaH to the N-naphthyl-2-hydroxybutyramide (VI). Acid hydrolysis of the amide function of (VI) gave diamine (VII). This was condensed with N-methyl iminodiacetic acid (VIII) using CDI in boiling THF to produce the piperazinedione (IX). After reduction of (IX) to the corresponding piperazine (X) with LiAlH4, the N-benzyl groups were cleaved by hydrogenolysis over Pd/C to afford the primary amine (XI). Finally, coupling of (XI) with 4-mo-pholinobenzoic (XII) acid using CDI provided the title amide.

The alkylation of (R)-2-amino-8-methoxy-1,2,3,4-tetrahydronaphthalene (I) with benzyl bromide provided the corresponding dibenzyl amine (II). After conversion of (II) to the hydrochloride salt, methyl ether cleavage by means of BBr3 at low temperature gave rise to naphthol (III). Condensation of (III) with 2-bromoisobutyramide (IV) yielded the naphthyloxybutyramide (V), which was rearranged at 130 C in the presence of NaH to the N-naphthyl-2-hydroxybutyramide (VI). Acid hydrolysis of the amide function of (VI) gave diamine (VII). This was condensed with N-methyl iminodiacetic acid (VIII) using CDI in boiling THF to produce the piperazinedione (IX). After reduction of (IX) to the corresponding piperazine (X) with LiAlH4, the N-benzyl groups were cleaved by hydrogenolysis over Pd/C to afford the primary amine (XI). Finally, coupling of (XI) with 4-mo-pholinobenzoic (XII) acid using CDI provided the title amide.

The alkylation of (R)-2-amino-8-methoxy-1,2,3,4-tetrahydronaphthalene (I) with benzyl bromide provided the corresponding dibenzyl amine (II). After conversion of (II) to the hydrochloride salt, methyl ether cleavage by means of BBr3 at low temperature gave rise to naphthol (III). Condensation of (III) with 2-bromoisobutyramide (IV) yielded the naphthyloxybutyramide (V), which was rearranged at 130 C in the presence of NaH to the N-naphthyl-2-hydroxybutyramide (VI). Acid hydrolysis of the amide function of (VI) gave diamine (VII). This was condensed with N-methyl iminodiacetic acid (VIII) using CDI in boiling THF to produce the piperazinedione (IX). After reduction of (IX) to the corresponding piperazine (X) with LiAlH4, the N-benzyl groups were cleaved by hydrogenolysis over Pd/C to afford the primary amine (XI). Finally, coupling of (XI) with 4-mo-pholinobenzoic (XII) acid using CDI provided the title amide.