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

HRID 2386928Notes

Reaction equation

HRID 2386928 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-326d74e1b1a24c22940bd03702b982c2
Source dataset
uspto-grants-2012_09
Patent number
US08268842B2

Reaction notes

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