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

HRID 630364

반응식

HRID 630364 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8075f9f261a34d23ab92d3c4414aad8c
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09315509B2

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