Benzoyl chloride → Ethyl 1-benzoyl-3-piperidinecarboxylate

HRID 1424569Notes

Reaction equation

HRID 1424569 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1.[C:12](Cl)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[C:12]([N:1]1[CH2:6][CH2:5][CH2:4][CH:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH2:2]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 98969Ethyl nipecotate

Product 1

HCID 3784394Ethyl 1-benzoyl-3-piperidinecarboxylateYield 90.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl piperidine-3-carboxylate (67.74 g, 266 mmol) in dry CH2Cl2 (300 mL) was added TEA (40.34 g, 399 mmol) at 0° C. Benzoyl chloride (41.13 g, 293 mmol) was added slowly to control any rise in reaction temperature. After addition was complete, the mixture was stirred at rt overnight. The mixture was washed with 1N aq HCl and brine. The organic layer was dried with anhydrous Na2SO4 and concentrated to leave a residue, which was purified by silica gel column chromatography (petroleum/ethyl acetate 5:1 to 3:1) to afford ethyl 1-benzoylpiperidine-3-carboxylate (62.63 g, 90%). 1H NMR (CD3OD, 400 MHz): δ=1.41 (t, 3H), 1.52 (m, 2H), 1.85 (m, 2H), 2.36 (s, 1H), 3.29 (m, 2H), 3.81 (m, 4H), 7.22 (m, 3H), 7.42 (m, 2H).

Workup

  1. customin reaction temperature
  2. additionAfter addition
  3. washThe mixture was washed with 1N aq HCl and brine
  4. dry with materialThe organic layer was dried with anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto leave a residue, which
  7. customwas purified by silica gel column chromatography (petroleum/ethyl acetate 5:1 to 3:1)

Sources & evidence

ORD record
ord-ff60b5a220994fa78a03a088407c5690
Source dataset
uspto-grants-2015_01
Patent number
US08927715B2

Reaction notes

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