반응식
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH:12]=O)=[CH:10][C:9]=1[F:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].ClCCl>C(Cl)(Cl)Cl.O.CO.ClCCl.CO>[NH3:1].[Br:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)=[CH:10][C:9]=1[F:16]참가 물질
반응물 4
생성물 2
시약·촉매·용매 4
반응 조건
- 온도
- 59 °C
실험 절차
A mixture of morpholine (0.215 ml, 2.46 mmol) and 4-bromo-3-fluorobenzaldehyde, available from Alfa Aesar, (500 mg, 2.46 mmol) was prepared in chloroform (8 ml) at room temperature and heated to 58-60° C. in a sealed tube for 1 h. The mixture was then cooled to room temperature and sodium triacetoxyborohydride (783 mg, 3.69 mmol) was added and the mixture heated again to 58-60° C. in a sealed tube for 12 h. The mixture was then allowed to cool to room temperature, diluted with water (4 ml), shaken vigorously and the mixture filtered through a phase separator and the filtrate concentrated in vacuo. The mixture was then purified by SCX-2 chromatography (Eluent: dichloromethane (2×10 ml), 10% methanol/dichloromethane (2×10 ml), methanol (2×10 ml), 7M NH3 in methanol/dichloromethane (2×10 ml) to afford 4-(4-bromo-3-fluorobenzyl)morpholine as a colourless oil (447 mg, 1.63 mmol, 66%).
후처리
- temperatureThe mixture was then cooled to room temperature
- temperaturethe mixture heated again to 58-60° C. in a sealed tube for 12 h
- temperatureto cool to room temperature
- filtrationthe mixture filtered through a phase separator
- concentrationthe filtrate concentrated in vacuo
- customThe mixture was then purified by SCX-2 chromatography (Eluent
출처 및 근거
- ORD 기록
- ord-b04c39a32f78474e804a11fcc2e8dc71
- 출처 데이터셋
- uspto-grants-2015_08
- 특허 번호
- US09115088B2
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