تفاعل #992767

ord-75f5224a09534d2a895eb05670122bcf

معادلة التفاعل

Cc1cc(N2CCOCC2)cc(C)c1N
2,6-Dimethyl-4-morpholin-4-yl-phenylamine
O=C(Cl)CC1CCCC1
cyclopentylacetyl chloride
O
Water
Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1
title compound
المردود 20.0%
Cc1cc(N2CCOCC2)cc(C)c1NC(=O)CC1CCCC1
2-Cyclopentyl-N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-acetamide
المردود 20.0%

المذيبات

ظروف التفاعل

درجة الحرارة
150°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    استخلاصthe product was extracted with ethyl acetate (3×25 mL)
  2. 2
    غسيلThe organic phases were washed with brine (50 mL)
  3. 3
    تجفيفdried over magnesium sulfate
  4. 4
    تركيزconcentrated in vacuo
  5. 5
    أخرىThe crude product was purified by flash chromatography

الإجراء التجريبي

2,6-Dimethyl-4-morpholin-4-yl-phenylamine (0.50 g) and cyclopentylacetyl chloride (0.53 mL) were dissolved in acetonitrile (5 mL) and heated to 150° C. for 10 minutes in a sealed microwave process vial. Water (25 mL) was added and the product was extracted with ethyl acetate (3×25 mL). The organic phases were washed with brine (50 mL), dried over magnesium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 0.138 g (20%) of the title compound as an off-white solid. LC-MS-TOF (m/z) 317 (MH+); tR=1.93, (UV, ELSD) 95%, 100%. 1H NMR (500 MHz, DMSO-d6): 1.21 (m, 2H), 1.52 (m, 2H), 1.61 (m, 2H), 1.76 (m, 2H), 2.07 (s, 6H), 2.11 (m, 1H), 2.25 (d, 2H), 3.05 (dd, 4H), 3.71 (dd, 4H), 6.63 (s, 2H), 8.94 (s, 1H).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08012962B2uspto-grants-2011_09