تفاعل #992772

معادلة التفاعل

2,6-diisopropyl-4-morpholin-4-yl-phenylamine

pyridine

cyclopentylacetyl chloride

→

title compound

المردود 33.0%

2-Cyclopentyl-N-(2,6-diisopropyl-4-morpholin-4-yl-phenyl)-acetamide

المردود 33.0%

المذيبات

tetrahydrofuran

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with 10% aqueous sodium bicarbonate (20 mL) and brine (20 mL)
2. 2
   تجفيفThe organic phase was dried over sodium sulfate
3. 3
   تركيزconcentrated in vacuo
4. 4
   أخرىpurified by flash chromatography
5. 5
   أخرىRecrystallisation of the crude brown material from hot ethyl acetate/heptane

الإجراء التجريبي

To a solution of 2,6-diisopropyl-4-morpholin-4-yl-phenylamine (279 mg) and pyridine (245 μL) in tetrahydrofuran (2 mL) was added cyclopentylacetyl chloride (210 mL) and the mixture was stirred for 1 hour at 25° C. The reaction mixture was diluted with ethyl acetate (20 mL) and washed with 10% aqueous sodium bicarbonate (20 mL) and brine (20 mL). The organic phase was dried over sodium sulfate, concentrated in vacuo and purified by flash chromatography. Recrystallisation of the crude brown material from hot ethyl acetate/heptane furnished 122 mg (33%) of the title compound as a white solid. LC-MS (m/z) 373 (MH+); tR=2.58, (UV, ELSD) 98%, 99%. 1H NMR (500 MHz, CDCl3): 1.19 (d, 12H), 1.27 (m, 2H), 1.60 (m, 2H), 1.68 (m, 2H), 1.93 (m, 2H), 2.40 (m, 1H), 2.41 (m, 2H), 3.05 (m, 2H), 3.17 (m, 4H), 3.87 (m, 4H), 6.49 (s, 1H), 6.70 (s, 2H).

المصدر