Hydrogen Bromide → 4-[2-(piperidin-1-yl)ethyl]phenol

HRID 1074426Notes

Reaction equation

HRID 1074426 reaction equation
[N:1]1([CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([O:15]C)=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br>C(O)(=O)C>[N:1]1([CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([OH:15])=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 21618620HCID 21618620, compound

Product 1

HCID 2611294-[2-(piperidin-1-yl)ethyl]phenol

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 11 g=50 mmoles of 4-(piperidin-1-ylethyl)-anisole in a mixture of 50 ml of glacial acetic acid and 50 ml of 48% strength hydrobromic acid is boiled under reflux for 4 hours, the solution is evaporated in vacuo and the residue is recrystallized from ethanol. This gives 9 g of the hydrobromide, melting point: 265° C. The salt is dissolved in 30 ml of water and the free base is precipitated with concentrated aqueous ammonia solution and is filtered off. This gives 5.5 g (54% of theory), melting point: 168°-169° C.

Workup

  1. temperatureunder reflux for 4 hours
  2. customthe solution is evaporated in vacuo
  3. customthe residue is recrystallized from ethanol
  4. dissolutionThe salt is dissolved in 30 ml of water
  5. customthe free base is precipitated with concentrated aqueous ammonia solution
  6. filtrationis filtered off

Sources & evidence

ORD record
ord-b74ceb59b9fe481c820a56cb79eeaeff
Source dataset
uspto-grants-1983_07
Patent number
US04391805

Reaction notes

Loading…