Formaldehyde → 4-Chloro-2-(piperidin-1-ylmethyl)phenol

HRID 1598315Notes

Reaction equation

HRID 1598315 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[CH2:9]=O.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 46844-ChlorophenolHCID 8082Piperidine

Product 1

HCID 2319084-Chloro-2-(piperidin-1-ylmethyl)phenol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chlorophenol (12.86 g), absolute ethanol (30 ml), formaldehyde (7.49 ml of a 37% aqueous solution) and piperidine (10.88 ml) was boiled under reflux for 4 hours. The mixture was evaporated to dryness and toluene (50 ml) was added. The mixture was evaporated to dryness and the residue was dissolved in 2M hydrochloric acid, washed with ethyl acetate, basified with concentrated sodium hydroxide solution and then extracted with dichloromethane to give 4-chloro-2-(piperidinomethyl)phenol as an oil which solidified on standing, m.p. 53°-56° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customThe mixture was evaporated to dryness and toluene (50 ml)
  3. additionwas added
  4. customThe mixture was evaporated to dryness
  5. dissolutionthe residue was dissolved in 2M hydrochloric acid
  6. washwashed with ethyl acetate
  7. extractionextracted with dichloromethane

Sources & evidence

ORD record
ord-fe18b909264b47e3aeffb2c067c35393
Source dataset
uspto-grants-1998_04
Patent number
US05736568

Reaction notes

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