تفاعل #1726710

معادلة التفاعل

4-piperidone

2-hydroxy-5-methoxybenzamide

morpholine

→

Compound 150

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

المذيبات

ethyl acetate

toluene

methanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis refluxed for 20 hr
2. 2
   غسيلwashed with water, brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   أخرىAfter solvent removal by rotoevaporation
5. 5
   أخرىthe crude product is purified by preparative TLC

الإجراء التجريبي

A mixture of 26 mg (0.083 mmol) of N-[4,8-dimethoxyquinoline-2-yl)carbonyl]-4-piperidone (prepared as described in Example 44), 14 mg (0.083 mmol) of 2-hydroxy-5-methoxybenzamide, and 0.020 mL of morpholine in a mixture of 0.2 mL of toluene and 0.6 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 17 mg (0.037 mmol, 45% yield) of 1′-[4,8-dimethoxyquinoline-2-yl)carbonyl]-6-methoxyspiro-[2H-1,3-benzoxazin-2,4′-piperidin]-4-(3H)-one (Compound 150): 1H NMR (DMSO-d6): δ 3.76 (s, 3H), 3.95 (s, 3H), 4.07 (s, 3H), 7.04 (d, 1H), 7.12 (d of d, 1H), 7.19 (s, 1H), 7.24 (m, 2H), 7.52 (d of d, 1H), 7.68 (d, 1H), and 8.85 ppm (s, 1H). MS m/z: 464.1 (M+H)+, 486.2 (M+Na)+.

المصدر