1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 1-Benzyl-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutyl azetidine-3-carboxamide

Beteiligte Stoffe

Reaktionsschritte

40 mg of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine was combined with 28 mg of 1-benzyl-azetidine-3-carboxylic acid in 5 ml dichloromethane. 38 mg of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride and 26 mg of dimethyl aminopyridine were added. The reaction solution was stirred at room temperature overnight. 5 ml of water was added and the mixture was extracted with 5 ml ethyl acetate three times. The organic layer was washed with saturated sodium bicarbonate, water and brine, dried over anhydrous sodium phosphate and concentrated under reduced pressure. The product was purified by column chromatography using 75% ethyl acetate in hexane as a resin: MS (m+1)=443.3; 1H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 1.95 (m, 1H), 2.05 (m, 1H), 2.25 (m, 2H), 2.95 (d, 1H), 3.00 (d, 1H), 3.40 (m, 1H), 3.45 (m, 1H), 3.50 (m, 1H), 3.65 (m, 2H), 3.75 (m, 2H), 4.25 (m, 2H), 4.35 (m, 2H), 4.50 (s, 1H), 6.5-7.0 (m, 2H), 7.1-7.4 (m, 5H).

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