4-(Piperidin-1-yl)phenol → HCID 21405650, compound

HRID 972890Notes

Reaction equation

HRID 972890 reaction equation
[Na].[N:2]1([C:8]2[CH:13]=[CH:12][C:11]([OH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Br[CH:16]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:17]([O:19]CC)=[O:18]>C(O)C>[C:22]1([CH:16]([O:14][C:11]2[CH:10]=[CH:9][C:8]([N:2]3[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]3)=[CH:13][CH:12]=2)[C:17]([OH:19])=[O:18])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 904524-(Piperidin-1-yl)phenolHCID 97780Ethyl bromophenylacetateHCID 5360545Sodium

Product 1

HCID 21405650HCID 21405650, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.3 g. of sodium is dissolved in 100 ml. of absolute ethanol; 17.7 g. of 4-piperidinophenol is introduced into the solution, and then 24.3 g. of ethyl α-bromophenylacetate is added dropwise thereto and the mixture refluxed for 10 hours. The reaction mixture is then evaporated, the residue mixed with water, and the aqueous solution extracted with ethyl acetate. The ethyl acetate solution is washed twice with dilute KOH and twice with water, then dried, and the solvent is evaporated, thus obtaining the ethyl ester of α-phenyl-α-4-piperidinophenoxy-acetic acid; hydrochloride, m.p. 149°-151°.

Workup

  1. temperaturethe mixture refluxed for 10 hours
  2. customThe reaction mixture is then evaporated
  3. additionthe residue mixed with water
  4. extractionthe aqueous solution extracted with ethyl acetate
  5. washThe ethyl acetate solution is washed twice with dilute KOH and twice with water
  6. customdried
  7. customthe solvent is evaporated

Sources & evidence

ORD record
ord-99c6fc8562064e6bad38c78bb67fceca
Source dataset
uspto-grants-1977_10
Patent number
US04053626

Reaction notes

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