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Morpholine → HCID 57318086, 화합물

HRID 843631
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인쇄 미리보기

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HRID 843631 반응식
[CH2:1]([C:4]1[CH:5]=[C:6](Br)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH3:3].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([C:4]1[CH:5]=[C:6]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH3:3]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 18414640HCID 18414640, 화합물

생성물 1

HCID 57318086HCID 57318086, 화합물수율 100.2%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 634876Binap, (A+-)-
촉매
HCID 1140Toluene용매

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온도
100 °C

실험 절차

A solution of 3-propyl-4-benzyloxy-1-bromobenzene (1.0 g, 3.3 mmol), morpholine (0.5 g, 6.6 mmol), Pd(OAc)2 (0.036 g, 0.16 mmol), BINAP (0.082 g, 0.132 mmol) and cesium carbonate (1.50 g, 4.62 mmol) in toluene (134 mL) was degassed and purged with nitrogen. The reaction mixture was stirred at 100° C. overnight. The reaction mixture was cooled to room temperature and partitioned between ethyl acetate and 10% aqueous citric acid. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate, filtered and evaporated to an oil. The resulting oil was chromatographed on silica gel, using toluene with 5% ethyl acetate, to afford the title compound (1.03 g).

후처리

  1. custompurged with nitrogen
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custompartitioned between ethyl acetate and 10% aqueous citric acid
  4. washThe organic layer was washed with water and brine
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated to an oil
  8. customThe resulting oil was chromatographed on silica gel

출처 및 근거

ORD 기록
ord-ce60c7cfda574e0a83ec5aaf797857ed
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06380191B1

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