Benzoyl chloride → Ethyl 1-benzoylpiperidine-4-carboxylate

HRID 1291194Notes

Reaction equation

HRID 1291194 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1.C(N(CC)CC)C.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1(C)C=CC=CC=1>[C:19]([N:1]1[CH2:6][CH2:5][CH:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:3][CH2:2]1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 735824Ethyl 1-benzoylpiperidine-4-carboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

18 ml (0.117 mol) of ethyl piperidine-4-carboxylate and 32.4 ml (0.2325 mol) of triethylamine were dissolved in 580 ml of toluene and treated with 18 ml (0.155 mol) of benzoyl chloride. The mixture was stirred at room temperature for 2 hrs., filtered and the solvent was evaporated. The residue was chromatographed on silica gel with ethyl acetate/hexane (1:3→1:1) as the eluent. 28.3 g (92%) of ethyl 1-benzoyl-4-piperidine-carboxylate were obtained as white crystal; m.p. 75°-78°.

Workup

  1. filtration, filtered
  2. customthe solvent was evaporated
  3. customThe residue was chromatographed on silica gel with ethyl acetate/hexane (1:3→1:1) as the eluent

Sources & evidence

ORD record
ord-deed3bc0dc9c4f7b91a9a5532fdb60ca
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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