2-Morpholinoethylamine → N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy)ethyl]-4-morpholineethanamine

HRID 16531

反応式

HRID 16531 の反応式
[N:1]1([CH2:7][CH2:8][NH2:9])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.I[CH2:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[O:28][CH:29]=[CH:30][N:31]=3)=[CH:23][CH:22]=2)=[CH:16][CH:15]=1>ClCCl>[O:28]1[CH:29]=[CH:30][N:31]=[C:27]1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([O:13][CH2:12][CH2:11][NH:9][CH2:8][CH2:7][N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)=[CH:19][CH:18]=2)=[CH:26][CH:25]=1

参加物

4

反応物 2

HCID 4082852-MorpholinoethylamineHCID 684895932-[4-[[4-(2-Iodoethoxy)phenyl]methyl]phenyl]oxazole

生成物 1

HCID 68488020N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy)ethyl]-4-morpholineethanamine収率 86.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2-(4-morpholinyl)ethanamine (1 g, 7.4 mmol) in dichloromethane was stirred as a solution of 2-[4-[[4-(2-iodoethoxy)phenyl]methyl]phenyl]oxazole (0.3 g, 0.74 mmol) in dichloromethane was added dropwise and the reaction was heated at reflux for 17 hours. The reaction was concentrated. The residue was dissolved in ethyl acetate and washed with water. The combined organic layers were dried and concentrated. Purification by chromatography on silica gel using a gradient of methanol in dichloromethane gave 0.26 g of N-[2-[4-[[4-(2-oxazolyl)phenyl]methyl]phenoxy]ethyl]-4-morpholineethanamine; 1H NMR (400 MHz, CDCl3) δ 7.97 (d, 2H), 7.68 (s, 1H), 7.27 (d, 2H), 7.21 (s, 1H), 7.13 (d, 2H), 6.82 (d, 2H), 4.08 (t, 2H), 3.96 (s, 2H), 3.67 (m, 4H), 3.03 (t, 2H), 2.78 (t, 2H), 2.51 (t, 2H), 2.43 (m, 4H) ppm.

後処理

  1. additionwas added dropwise
  2. temperaturethe reaction was heated
  3. temperatureat reflux for 17 hours
  4. concentrationThe reaction was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with water
  7. customThe combined organic layers were dried
  8. concentrationconcentrated
  9. customPurification by chromatography on silica gel using a gradient of methanol in dichloromethane

出典と根拠

ORDレコード
ord-cd78fef494c0437599027399df58753d
出典データセット
uspto-grants-2010_06
特許番号
US07737145B2

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