Tetrahydrofuran → 4-[(1-Methyl-3-piperidinyl)oxy]benzenamine

HRID 1988986노트

반응식

HRID 1988986 반응식
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1COCC1.[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([OH:23])[CH2:18]1.F[C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][CH:26]=1>CCO.[Pd].O>[CH3:16][N:17]1[CH2:22][CH2:21][CH2:20][CH:19]([O:23][C:25]2[CH:30]=[CH:29][C:28]([NH2:31])=[CH:27][CH:26]=2)[CH2:18]1

참가 물질

8

반응물 4

HCID 8028TetrahydrofuranHCID 9590p-FluoronitrobenzeneHCID 980163-Piperidinol, 1-methyl-HCID 3251421Potassium bis(trimethylsilyl)amide

생성물 1

HCID 220554854-[(1-Methyl-3-piperidinyl)oxy]benzenamine

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

KHMDS (1.1 equivalent) was added to a THF solution of 1-methylpiperidin-3-ol (1 equivalent) at 0° C. and stirred until H2 evolution ceased. 1-fluoro-4-nitrobenzene (1 equivalent) was then added and the solution was allowed to warm to room temperature. After 2 hours, water was added and the mixture was extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, and concentrated in vacuo to give a bright yellow oil which was directly used in the reduction step. The oil (1 equivalent) and a catalytic amount of 10% Pd/C were suspended in anhydrous EtOH at room temperature. The reaction flask was evacuated and subsequently filled with H2. After stirring for 18 hours, the mixture was filtered through Celite, and the solvent was concentrated in vacuo to yield 4-(1-methyl-3-piperidyloxy)phenylamine. LC/MS (m/z) 207.2 (MH+), Rt 0.47 minutes.

후처리

  1. extractionthe mixture was extracted with EtOAc (3×)
  2. dry with materialThe combined organic extracts were dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customto give a bright yellow oil which
  5. customThe reaction flask was evacuated
  6. additionsubsequently filled with H2
  7. stirringAfter stirring for 18 hours
  8. filtrationthe mixture was filtered through Celite
  9. concentrationthe solvent was concentrated in vacuo

출처 및 근거

ORD 기록
ord-559ac06826b543abb4bd37d50fd376e6
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07642278B2

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