Réaction #1726710

Équation de réaction

4-piperidone

2-hydroxy-5-methoxybenzamide

morpholine

→

Compound 150

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

Solvants

ethyl acetate

toluene

methanol

Conditions de réaction

Traitement

1. 1
   Températureis refluxed for 20 hr
2. 2
   Lavagewashed with water, brine
3. 3
   Séchagedried over Na2SO4
4. 4
   AutreAfter solvent removal by rotoevaporation
5. 5
   Autrethe crude product is purified by preparative TLC

Mode opératoire

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)+.

Source