Cesium carbonate → 4-Benzyl-2-[4-(2,6-dimethyl-phenylsulfanyl)-phenyl]-morpholine

HRID 571783노트

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HRID 571783 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17](Br)=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=1[SH:29].N1C2C(=CC=CC=2O)CCC1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.O>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([S:29][C:23]3[C:24]([CH3:28])=[CH:25][CH:26]=[CH:27][C:22]=3[CH3:21])=[CH:16][CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 610452,6-DimethylthiophenolHCID 2414901,2,3,4-Tetrahydroquinolin-8-olHCID 580978794-Benzyl-2-(4-bromo-phenyl)-morpholine

생성물 1

HCID 666546634-Benzyl-2-[4-(2,6-dimethyl-phenylsulfanyl)-phenyl]-morpholine수율 68.2%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
130 °C

실험 절차

To a solution of 4-benzyl-2-(4-bromo-phenyl)-morpholine (2.00 g; 6.02 mmol) and 2,6-dimethylthiophenol (0.88 mL; 6.62 mmol) in DMF (15 mL) was added CuBr (0.43 g; 3.01 mmol), 1,2,3,4-tetrahydro-quinolin-8-ol (0.45 g; 3.01 mmol) and Cs2CO3 (2.45 g; 7.52 mmol; 1.25 eq.). The resulting mixture was heated, in a closed vessel, at 130° C., for 2 days. After cooling to RT, water was added and the mixture extracted with Et2O. The combined organic layers were washed with water, dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by column chromatography (Et2O/hexanes 1:1) to afford 4-benzyl-2-[4-(2,6-dimethyl-phenylsulfanyl)-phenyl]-morpholine (1.60 g).

후처리

  1. temperatureAfter cooling to RT
  2. extractionthe mixture extracted with Et2O
  3. washThe combined organic layers were washed with water
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography (Et2O/hexanes 1:1)

출처 및 근거

ORD 기록
ord-3fb24419b9f841bdbfe0614453d8891a
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09029371B2

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