Water → 1-(3-Methoxyphenyl)cyclohexan-1-amine

HRID 852633노트

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HRID 852633 반응식
[N:1]([C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH3:17])[CH:11]=2)[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].O>C1COCC1>[CH3:17][O:16][C:12]1[CH:11]=[C:10]([C:4]2([NH2:1])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]2)[CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 866028821-(1-Azidocyclohexyl)-3-(methyloxy)benzene

생성물 1

HCID 361337791-(3-Methoxyphenyl)cyclohexan-1-amine수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-(1-azidocyclohexyl)-3-(methyloxy)benzene (D315) (2.78 g, 12.0 mmol, 1 equiv) in THF (20 ml) at room temperature was added LiAlH4 (1M in THF, 36 ml, 36 mmol, 3 equiv) and the resulting mixture was stirred at this temperature for 4 h. The mixture was then carefully quenched with a 1N aqueous NaOH solution (6 ml, 60 mmol, 1 equiv) then H2O. The mixture was filtered through a pad of celite then acidified with a 2N aqueous HCl solution (50 ml). The two layers were separated and the pH of the aqueous phase adjusted to 9 using a 2N aqueous NaOH solution. The aqueous phase was extracted three times with Et2O and the combined organic phase were dried over MgSO4 then concentrated in vacuo to give {1-[3-(methyloxy)phenyl]cyclohexyl}amine (F41) (1.55 g, 63%) as a clear oil which was used in the next step without further purification. [M+H]+=189.0, RT=1.90 min.

후처리

  1. filtrationThe mixture was filtered through a pad of celite
  2. customThe two layers were separated
  3. extractionThe aqueous phase was extracted three times with Et2O
  4. dry with materialthe combined organic phase were dried over MgSO4
  5. concentrationthen concentrated in vacuo

출처 및 근거

ORD 기록
ord-470a17aad2384d3086f478e5ba41633c
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253198B2

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