Sodium Hydroxide → HCID 9811366, compound

Participants

Reaction Steps

Triethylamine (6.7 ml) was added dropwise to a suspension of 4-amino-1-(3-phenylpropyl)piperidine dihydrochloride (7.01 g) and dimethylformamide (40 ml). The mixture was stirred for 10 minutes. 5-Thia-1,8b-diazaacenaphthylene-4-carboxylic acid (5.00 g), 1-hydroxy-1H-benzotriazole monohydrate (0.710 g) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide (4.61 g) were added into the reaction mixture. This was stirred for 2 hours at 68-70° C. (inner temperature). Ethyl acetate:tetrahydrofuran=4:1 (380 ml), 1N-sodium hydroxide (50 ml) and water (80 ml) were added into the reaction solution. The aqueous layer was extracted by ethyl acetate:tetrahydrofuran=4:1 (120 ml×2). The organic layer was washed with water (130 ml×3), and then concentrated. The residue which was added ethyl acetate (15 ml) was stirred for 2 hours at room temperature. The reaction mixture was dried under reduced pressure to obtain N-[1-(3-phenylpropan-1-yl)piperidin-4-yl]-5-thia-1,8b-diazaacenaphthylene-4-carboxamide (8.87 g, 92.5%).

Provenance & Evidence