4-(3-Methoxyphenyl)piperidine → 4-(3-Hydroxyphenyl)piperidine

HRID 1070727Notes

Reaction equation

HRID 1070727 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][CH:8]=1>Br>[NH:12]1[CH2:13][CH2:14][CH:9]([C:5]2[CH:4]=[C:3]([OH:2])[CH:8]=[CH:7][CH:6]=2)[CH2:10][CH2:11]1

Participants

3

Reactant 1

HCID 107028904-(3-Methoxyphenyl)piperidine

Product 1

HCID 105834534-(3-Hydroxyphenyl)piperidine

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Conditions

Temperature
120 °C

Procedure

4-(3-Methoxy-phenyl)-piperidine (1.7 g) was dissolved in 48-% HBr (60 ml) and stirred at 120° C. under an Argon-atmosphere for 3 h. The excess of HBr was then evaporated and absolute ethanol added and evaporated. This procedure was repeated several times to yield dry crystals of 3-piperidin-4-yl-phenol×HBr (2.3 g). MS m/z (relative intensity, 70 eV) 177 (M+, bp), 176 (23), 91 (14), 57 (44), 56 (60).

Workup

  1. customThe excess of HBr was then evaporated
  2. additionabsolute ethanol added
  3. customevaporated
  4. customto yield
  5. dry with materialdry crystals of 3-piperidin-4-yl-phenol×HBr (2.3 g)

Sources & evidence

ORD record
ord-e297217984d14d93898d33242c0f519d
Source dataset
uspto-grants-2005_06
Patent number
US06903120B2

Reaction notes

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