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Cesium carbonate → 4-Benzyl-2-[3-chloro-4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine

HRID 920545
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HRID 920545 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([Cl:21])[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:22][C:23]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:24]=1[CH2:25]Br.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:25][C:24]3[C:23]([Cl:22])=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:31])=[C:16]([Cl:21])[CH:15]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 301591-Bromomethyl-2,6-dichlorobenzeneHCID 666540724-(4-Benzyl-morpholin-2-yl)-2-chloro-phenol

생성물 1

HCID 670325214-Benzyl-2-[3-chloro-4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine수율 102.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 4-(4-benzyl-morpholin-2-yl)-2-chloro-phenol (0.50 g; 1.56 mmol), 2,6-dichlorobenzyl bromide (0.39 g; 1.64 mmol) and Cs2CO3 (2.55 g; 7.82 mmol) in CH3CN (20 mL) was heated under reflux overnight. After cooling to RT the resulting mixture was partitioned between EtOAc and water. The layers were separated and the organic layer, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by column chromatography (SiO2, CH2Cl2:MeOH 98:2) to afford 4-benzyl-2-[3-chloro-4-(2,6-dichloro-benzyloxy)-phenyl]-morpholine (0.74 g)

후처리

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customwas partitioned between EtOAc and water
  4. customThe layers were separated
  5. dry with materialthe organic layer, dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography (SiO2, CH2Cl2:MeOH 98:2)

출처 및 근거

ORD 기록
ord-96f1fa474f904cc498901d23f01e07b4
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09273017B2

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