Benzyl Chloride → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 1655962Notes

Reaction equation

HRID 1655962 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-]>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 19660Carbonate IonHCID 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 potassrum 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 (3x), 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 (3x)
  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-2bfae8d901874a4fa6d97c768cd08eeb
Source dataset
uspto-grants-1993_10
Patent number
US05252586

Reaction notes

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