反応 #1726709

反応方程式

4-piperidone

5-acetamido-2-hydroxybenzamide

morpholine

→

Compound 9

spiro[2H-1,3-benzoxazin-2,4′-piperidin]-4-(3H)-one

溶媒

ethyl acetate

methanol

反応条件

後処理

1. 1
   温度is refluxed for 48 hr
2. 2
   洗浄washed with water, brine
3. 3
   乾燥dried over Na2SO4
4. 4
   その他After solvent removal by rotoevaporation
5. 5
   その他the crude product is purified by preparative TLC

実験手順

A mixture of 24 mg (0.077 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone, 15 mg (0.077 mmol) of 5-acetamido-2-hydroxybenzamide, and 0.020 mL of morpholine in 3 mL of methanol is refluxed for 48 hr. The reaction mixture is diluted with ethyl acetate, and washed with water, brine, and dried over Na2SO4. After solvent removal by rotoevaporation, the crude product is purified by preparative TLC to give 11 mg (0.022 mmol, 30% yield) of 6-acetamido-1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]spiro[2H-1,3-benzoxazin-2,4′-piperidin]-4-(3H)-one (Compound 9): 1H NMR (DMSO-d6): δ 2.02 (s, 3H), 3.95 (s, 3H), 4.06 (s, 3H), 7.03 (d, 1H), 8.19 (s, 1H), 7.24 (d of d, 1H), 7.52 (d of d, 1H), 7.67 (m, 2H), 8.02 (d, 1H), 8.82, (s, 1H) and 9.98 ppm (s, 1H). MS m/z: 491.1 (M+H)+, 513.2 (M+Na)+.

出典