反応 #1726711

反応方程式

4-piperidone

2-hydroxy-5-methylbenzamide

morpholine

→

Compound 137

6-methylspiro-[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 20 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 26 mg (0.083 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone (prepared as described in Example 44), 12.5 mg (0.083 mmol) of 2-hydroxy-5-methylbenzamide, and 0.020 mL of morpholine in 2 mL of methanol is refluxed for 20 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 20 mg (0.045 mmol, 54% yield) of 1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]-6-methylspiro-[2H-1,3-benzoxazin-2,4′-piperidin]-4-(3H)-one (Compound 137): 1H NMR (DMSO-d6): δ 2.28 (s, 3H), 3.95 (s, 3H), 4.06 (s, 3H), 6.98 (d, 1H), 7.19 (s, 1H), 7.23 (d of d, 1H), 7.33 (d of d, 1H), 7.52 (d of d, 1H), 7.56 (d, 1H), 7.68 (d of d, 1H), and 8.77 ppm (s, 1H). MS m/z: 448.1 (M+H)+, 470.0 (M+Na)+.

出典