Triethylamine → Ethyl 1-(3-chlorobenzoyl)-4-piperidinecarboxylate

HRID 20266

Reaction equation

HRID 20266 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.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=[O:17].C(N(CC)CC)C>ClCCl>[CH2:8]([O:7][C:5]([CH:4]1[CH2:3][CH2:2][N:1]([C:16](=[O:17])[C:15]2[CH:19]=[CH:20][CH:21]=[C:13]([Cl:12])[CH:14]=2)[CH2:11][CH2:10]1)=[O:6])[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69252Benzoyl chloride, 3-chloro-HCID 70770Ethyl 4-piperidinecarboxylate

Product 1

HCID 798973Ethyl 1-(3-chlorobenzoyl)-4-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of ethyl isonipecotate (27.6 g, 175 mmol) in dichloromethane (50 ml) was added dropwise over 10 minutes to a solution of 3-chlorobenzoyl chloride (20 ml, 160 mmol) and triethylamine (28 ml, 200 mmol) in dichloromethane (500 ml) cooled to between 10 and 15° C. The reaction was then stirred at room temperature for 3 hours and concentrated under reduced pressure. The residue was diluted with ether, the solution washed with 1N hydrochloric acid, sodium carbonate solution (×3) and brine. It was then dried over MgSO4 and evaporated under reduced pressure, to give the title compound as a solid, 44.49.

Workup

  1. temperaturecooled to between 10 and 15° C
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with ether
  4. washthe solution washed with 1N hydrochloric acid, sodium carbonate solution (×3) and brine
  5. dry with materialIt was then dried over MgSO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9930678f962847d1aa3e1e730e0a3dbf
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

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