1-Bromohexane → N-Hexyl-4-(3-hydroxyphenyl)piperidine
Reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:8]=[C:9]([OH:13])[CH:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>CN(C)C=O.O>[CH2:20]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([OH:13])[CH:8]=2)[CH2:3][CH2:2]1)[CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of 3-(4-piperidinyl)phenol (Preparation 47, 376 mg, 2.12 mmol) in N,N-dimethylformamide (5 ml) was added sodium hydrogen carbonate (267 mg, 3.18 mmol) and 1-bromohexane (0.36 ml, 2.55 mmol). The reaction mixture was heated at 100° C. for 4 h. The reaction mixture was then diluted with water (20 ml) and extracted with diethyl ether (3×10 ml). The combined organic extracts were dried (MgSO4), filtered and concentrated in vacuo to give the title compound as an oil which was not purified further (500 mg, 89%).
Workup
- extractionextracted with diethyl ether (3×10 ml)
- dry with materialThe combined organic extracts were dried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-2df710aab9a74073adcc30fd27833e75
- Source dataset
- uspto-grants-2003_08
- Patent number
- US06610711B2
Reaction notes
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