4-Nitrophenol → 1-[3-(4-Nitrophenoxy)propyl]piperidine

HRID 2111820노트

반응식

HRID 2111820 반응식
[N:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[N+:11]([C:14]1[CH:19]=[CH:18][C:17](O)=[CH:16][CH:15]=1)([O-:13])=[O:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[N+:11]([C:14]1[CH:19]=[CH:18][C:17]([O:10][CH2:9][CH2:8][CH2:7][N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:16][CH:15]=1)([O-:13])=[O:12]

참가 물질

6

반응물 4

HCID 9804-NitrophenolHCID 11776TriphenylphosphineHCID 66032Piperidine-1-propanolHCID 75555Diisopropyl diazene-1,2-dicarboxylate

생성물 1

HCID 20579281-[3-(4-Nitrophenoxy)propyl]piperidine

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

3-piperidin-1-yl-propan-1-ol (3.66 g, 25.6 mmol), 4-nitrophenol (2.96 g, 21.3 mmol) and triphenylphosphine (6.71 g, 25.6 mmol) were dissolved in dry tetrahydrofuran in a current of nitrogen, and cooled on the ice bath. Diisopropyl azodicarboxylate (5.0 mL, 25.6 mmol) was dripped in, and stirred at room temperature for 40 hours. The reaction liquid was concentrated, diethyl ether was added, and the solid precipitate was filtered off. The filtrate was concentrated, the product purified by silica gel column chromatography (chloroform/methanol=100/0-95/5), and the target substance (3.49 g, 62%) was thus obtained as a light yellow oily residue.

후처리

  1. customThe reaction liquid
  2. concentrationwas concentrated
  3. additiondiethyl ether was added
  4. filtrationthe solid precipitate was filtered off
  5. concentrationThe filtrate was concentrated
  6. customthe product purified by silica gel column chromatography (chloroform/methanol=100/0-95/5)
  7. customthe target substance (3.49 g, 62%) was thus obtained as a light yellow oily residue

출처 및 근거

ORD 기록
ord-fd1f43e6d5b44092a867a8b544008cd4
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521455B2

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