Water → 3-(piperidin-1-yl)phenol

HRID 2066391Notes

Reaction equation

HRID 2066391 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)phenol

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Aminophenol (500 mg) was dissolved in toluene (5.0 ml), the solution was added with sodium hydrogencarbonate (846.5 mg) and 1,5-dibromopentane (686.3 μl) at room temperature, and the mixture was stirred for 16 hours under reflux by heating. The reaction mixture was cooled, and then added with distilled water and ethyl acetate for extraction, and the organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain the title compound (513 mg).

Workup

  1. temperatureunder reflux
  2. temperatureby heating
  3. temperatureThe reaction mixture was cooled
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1cde0ed98c63437e97ffc70cb0eaad3d
Source dataset
uspto-grants-2012_10
Patent number
US08293715B2

Reaction notes

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