Water → 2-Cyclopentyl-N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-acetamide

HRID 1867301

反応式

HRID 1867301 の反応式
[CH3:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([CH3:14])[C:3]=1[NH2:15].[CH:16]1([CH2:21][C:22](Cl)=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1.O>C(#N)C>[CH:16]1([CH2:21][C:22]([NH:15][C:3]2[C:2]([CH3:1])=[CH:7][C:6]([N:8]3[CH2:13][CH2:12][O:11][CH2:10][CH2:9]3)=[CH:5][C:4]=2[CH3:14])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17]1

参加物

5

反応物 3

HCID 962WaterHCID 3485182Cyclopentylacetyl chlorideHCID 230094142,6-Dimethyl-4-morpholin-4-yl-phenylamine

生成物 1

HCID 116453782-Cyclopentyl-N-(2,6-dimethyl-4-morpholin-4-yl-phenyl)-acetamide収率 20%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
150 °C

実験手順

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).

後処理

  1. extractionthe product was extracted with ethyl acetate (3×25 mL)
  2. washThe organic phases were washed with brine (50 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-98da6bcd28a44166b372fae1d85adb97
出典データセット
uspto-grants-2009_12
特許番号
US07632835B2

関連ノート

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