Benzyl Chloride → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 1034414Notes

Reaction equation

HRID 1034414 reaction equation
[NH:1]1[CH2:11][CH2:10][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:3][CH2:2]1.[CH2:12](Cl)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+]>CCO>[CH2:12]([N:1]1[CH2:2][CH2:3][CH:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH2:10][CH2:11]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 90423Ethyl 1-benzylpiperidine-4-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl isonipecotate (212 g, 1 35 mole), benzyl chloride (170 g, 1.35 mole), and potassium carbonate (322 g, 233 mole) were stirred at room temperature in absolute EtOH (1.8 L) for 72 hours. The crude mixture was filtered through Celite, rinsed with Et2O, and concentrated in vacuo. The resulting mixture was diluted with Et2O, and extracted with H2O (3×), then brine, dried (MgSO4), and concentrated in vacuo. The product was distilled under high vacuum, bp 128°-130° C. at 0.8 mm Hg, to yield 252 g of a colorless liquid (76%). Analysis: Calculated for C15H21NO2 : C,72.84; H,8.56; N,5.66; found: C,72.91; H,8.38; N,5.88

Workup

  1. filtrationThe crude mixture was filtered through Celite
  2. washrinsed with Et2O
  3. concentrationconcentrated in vacuo
  4. additionThe resulting mixture was diluted with Et2O
  5. extractionextracted with H2O (3×)
  6. dry with materialbrine, dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. distillationThe product was distilled under high vacuum, bp 128°-130° C. at 0.8 mm Hg

Sources & evidence

ORD record
ord-f8c2dd80b6f943ccb035cc578a56bd52
Source dataset
uspto-grants-1994_05
Patent number
US05317024

Reaction notes

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