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Water → 4-(4-Benzyl-[1,4]oxazepan-6-yl)-benzonitrile

HRID 515471
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HRID 515471 반응식
[CH2:1]([N:8]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:12][O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].O.[CH3:29][N:30]1CCCC1=O>[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.O.O.O.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([N:8]1[CH2:14][CH:13]([C:15]2[CH:20]=[CH:19][C:18]([C:29]#[N:30])=[CH:17][CH:16]=2)[CH2:12][O:11][CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

8

반응물 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 667185934-Benzyl-6-(4-bromo-phenyl)-[1,4]oxazepane

생성물 1

HCID 667184644-(4-Benzyl-[1,4]oxazepan-6-yl)-benzonitrile수율 79%

시약·촉매·용매 3

HCID 161067
Potassium ferrocyanide trihydrate
촉매
HCID 167845palladium(II) acetate촉매
HCID 15826098Cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;iron(2+)촉매

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온도
120 °C

실험 절차

A mixture of 4-benzyl-6-(4-bromo-phenyl)-[1,4]oxazepane (2.4 g, 6.9 mmol), potassium hexacyanoferrate(II) trihydrate (1.48 g, 3.5 mmol), palladium(II) acetate (1.6 mg, 0.007 mmol), diphenylphosphinoferrocene (7.8 mg, 0.014 mmol) and sodium carbonate (0.74 g, 7.0 mmol) in N-methylpyrrolidone (NMP) (7 mL) was prepared in a round bottom flask at room temperature under nitrogen atmosphere and the mixture was heated to 120° C. After stirring for 10 hours, the reaction mixture was cooled to room temperature and poured into water. The organic materials were extracted with ethyl acetate and wash with brine. The organic layer was separated and dried over anhydrous sodium sulfate. After concentration, the residual oil was passed through flash column chromatography on silica gel (hexane/ethyl acetate=90/10 to 50/50 as an eluant) to obtain pure 4-(4-benzyl-[1,4]oxazepan-6-yl)-benzonitrile (1.6 g, 5.5 mmol, 79%) as light yellow oil.

후처리

  1. customwas prepared in a round bottom flask at room temperature under nitrogen atmosphere
  2. temperaturethe reaction mixture was cooled to room temperature
  3. extractionThe organic materials were extracted with ethyl acetate
  4. washwash with brine
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationAfter concentration

출처 및 근거

ORD 기록
ord-72baefa755f9490182f1e5ccffd16f2f
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108957B2

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