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Ammonium Chloride → 1-Azido-1,1-bis(4-fluorophenyl)-2-propaneamine

HRID 1829879
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인쇄 미리보기

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HRID 1829879 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:10]([CH3:11])[NH:9]2)=[CH:4][CH:3]=1.[N-:19]=[N+:20]=[N-:21].[Na+].[Cl-].[NH4+]>CO.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)([NH2:19])[CH:10]([NH2:9])[CH3:11])=[CH:4][CH:3]=1.[N:19]([C:8]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[CH:10]([NH2:9])[CH3:11])=[N+:20]=[N-:21]
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참가 물질

8

반응물 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 220548312,2-Bis(4-fluorophenyl)-3-methylaziridine

생성물 2

HCID 218859191,1-Bis(4-fluorophenyl)-1,2-propanediamineHCID 220548071-Azido-1,1-bis(4-fluorophenyl)-2-propaneamine수율 124.9%

시약·촉매·용매 3

HCID 887
Methanol
용매
HCID 962Water용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

The above-mentioned aziridine compound (342 mg) was dissolved in mixture of methanol (10 mL) and water (2 mL), and sodium azide (439 mg) and ammonium chloride (155 mg) were added to the solution. The mixture was stirred at 60° C. for 40 hours. After the reaction mixture was cooled by standing, the reaction mixture was diluted with ethyl acetate, and the dilution was washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution in this order, dried over anhydrous sodium sulfate, and concentrated in vacuo. The obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=2:1→1:1) to give the desired compound, 1-azido-1,1-bis(4-fluorophenyl)-2-propaneamine (251 mg). The above-mentioned azide compound (8 mg) was reduced in the presence of 10% palladium carbon catalyst (5 mg) in methanol under 1 atm hydrogen at room temperature. The catalyst was removed by filtration, and then the filtrate was concentrated in vacuo to give the title compound (7 mg).

후처리

  1. additionwere added to the solution
  2. temperatureAfter the reaction mixture was cooled
  3. washthe dilution was washed with saturated sodium hydrogen carbonate aqueous solution, water and saturated sodium chloride aqueous solution in this order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by silica gel column chromatography (C-300; hexane:ethyl acetate=2:1→1:1)

출처 및 근거

ORD 기록
ord-7fa7f25e5749455cb3dcde88ba290724
출처 데이터셋
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07064142B2

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