4-(3-Methoxyphenyl)piperidine → 4-(3-Hydroxyphenyl)piperidine
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]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
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
- customThe excess of HBr was then evaporated
- additionabsolute ethanol added
- customevaporated
- customto yield
- dry with materialdry crystals of 3-piperidin-4-yl-phenol×HBr (2.3 g)
Sources & evidence
- ORD record
- ord-4a987e1ffdd34657b2887579273812da
- Source dataset
- uspto-grants-2008_08
- Patent number
- US07417043B2
Reaction notes
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