Ethyl 1-benzylpiperidine-4-carboxylate → (1-Benzylpiperidin-4-yl)methanol
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](OCC)=[O:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>CCOCC>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][OH:15])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 1-benzyl-4-carboethoxypiperidine (74.3 g, 0.300 mole) in anhydrous Et2O (740 mL) was stirred at 0° C. under N2. Lithium aluminum hydride (11.4 g, 0.300 mole) was added in small portions over 0.5 hours. After an additional 2.5 hours, the reaction was carefully quenched with H2O (740 mL). The mixture was filtered through a Celite pad and rinsed with ethyl acetate (EtOAc), then the layers were separated. The aqueous layer was saturated with NaCl, then extracted with EtOAc (3×100 mL). The combined organics were extracted with brine, dried (MgSO4), and concentrated in vacuo. The resulting crude product was vacuum distilled, bp ~144° C. at 0.1 mm Hg, to yield the alcohol (55.8 g,91%) as a colorless, viscous oil. Analysis: Calculated for C13H19NO: C,76.06; H,9.33; N,6.82; found: C,75.87; H,9.16; N,6.55.
Workup
- customthe reaction was carefully quenched with H2O (740 mL)
- filtrationThe mixture was filtered through a Celite pad
- washrinsed with ethyl acetate (EtOAc)
- customthe layers were separated
- extractionextracted with EtOAc (3×100 mL)
- extractionThe combined organics were extracted with brine
- dry with materialdried (MgSO4)
- concentrationconcentrated in vacuo
- distillationdistilled
Sources & evidence
- ORD record
- ord-689c0faf1a504ffab9037de04715d7c1
- Source dataset
- uspto-grants-1993_10
- Patent number
- US05252586
Reaction notes
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