Benzyl Chloride → Ethyl 1-benzylpiperidine-4-carboxylate

HRID 1681177Notes

Reaction equation

HRID 1681177 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+]>C(O)C>[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

A mixture of ethyl isonipecotate (212 g, 1.35 mol), benzyl chloride (170 g, 1.35 mol) and potassium carbonate (322 g, 2.33 mol) in absolute ethanol (1.8 L) was stirred mechanically at room temperature for 72 h. Solvent was removed in vacuo and the residue was dissolved in water and then extracted with ether three times. The combined organic layers were dried over magnesium sulfate, filtered and solvent was removed in vacuo to give a pale yellow oil. Vacuum distillation (b.p. 134°-136° C., 1.0 Torr) gave a colorless liquid (252 g, 76% yield): 'H-NMR: 7.30-7.22 (m, 5H), 4.12 (q, 2H, J=7), 3.48 (s, 2H), 2.88-2.82 (m, 2H), 2.33-2.19 (m, 1H), 2.08-1.67 (m, 6H), 1.24 (t, 3H, J=7); Anal.: Calcd. for C15H21NO2 : C,72.84, H,8.56, N,5.66; Found: C,72.91, H,8.38, N,5.88.

Workup

  1. customSolvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ether three times
  4. dry with materialThe combined organic layers were dried over magnesium sulfate
  5. filtrationfiltered
  6. customsolvent was removed in vacuo
  7. customto give a pale yellow oil
  8. distillationVacuum distillation (b.p. 134°-136° C., 1.0 Torr)

Sources & evidence

ORD record
ord-9ef3191b55d5489f914f3778098474fd
Source dataset
uspto-grants-1992_12
Patent number
US05169855

Reaction notes

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