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

HRID 2111820ノート

反応式

HRID 2111820 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-fd1f43e6d5b44092a867a8b544008cd4
出典データセット
uspto-grants-2009_04
特許番号
US07521455B2

反応ノート

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