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

HRID 1483914Notes

Reaction equation

HRID 1483914 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-4039d1f6ed974db3835e5a5f83309e8e
Source dataset
uspto-grants-2016_08
Patent number
USRE046117E1

Reaction notes

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