Water → 3-(piperidin-1-yl)phenol

HRID 1516144Notes

Reaction equation

HRID 1516144 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)(O)[O-].[Na+].Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br.O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:1]1([C:2]2[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=2)[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 962WaterHCID 81001,5-DibromopentaneHCID 115683-AminophenolHCID 516892Sodium Bicarbonate

Product 1

HCID 2298553-(piperidin-1-yl)phenolYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

10.91 g (100 mmol) of 3-aminophenol was dissolved in 100 ml of toluene, and 18.5 g (220 mmol) of sodium bicarbonate and 16.0 ml (110 mmol) of 1,5-dibromopentane were added thereto, followed by refluxing the resulting mixture for 17 hours. The reaction mixture was cooled to room temperature, and 100 ml of water and 100 ml of ethyl acetate were added thereto. The water layer was separated, extracted twice with 100 ml portions of ethyl acetate, and the organic layers were combined, dried over anhydrous MgSO4, and concentrated under a reduced pressure. The concentrate was subjected to column chromatography using 20% ethyl acetate/hexane as an eluent to obtain 12.9 g (yield 73%) of 3-(piperidin-1-yl)phenol as a solid.

Workup

  1. temperatureby refluxing the resulting mixture for 17 hours
  2. customThe water layer was separated
  3. extractionextracted twice with 100 ml portions of ethyl acetate
  4. dry with materialdried over anhydrous MgSO4
  5. concentrationconcentrated under a reduced pressure

Sources & evidence

ORD record
ord-c3b3bf78f1c746b1b065eaf16d72e4b1
Source dataset
uspto-grants-2012_07
Patent number
US08227456B2

Reaction notes

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