Benzoyl chloride → (2S)-N,N-dimethyl-1-(phenylcarbonyl)-2-piperidinecarboxamide

HRID 1366700Notes

Reaction equation

HRID 1366700 reaction equation
Cl.[CH3:2][N:3]([CH3:12])[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][NH:7]1)=[O:5].C(=O)(O)[O-].[Na+].[C:18](Cl)(=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)Cl.O>[CH3:2][N:3]([CH3:12])[C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][N:7]1[C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:25])=[O:5]

Participants

6

Reactant 3

HCID 7412Benzoyl chlorideHCID 516892Sodium BicarbonateHCID 66936649(2S)-N,N-dimethyl-2-piperidinecarboxamide hydrochloride

Product 1

HCID 66936735(2S)-N,N-dimethyl-1-(phenylcarbonyl)-2-piperidinecarboxamideYield 74.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

(2S)—N,N-Dimethyl-2-piperidinecarboxamide hydrochloride (880 mg, 4.567 mmol) was dissolved in a mixture of CH2Cl2 (15 mL) and water (15 mL), and then solid sodium bicarbonate (1.534 g, 18.268 mmol) was added, followed by benzoyl chloride (0.556 mL, 4.795 mmol). After stirring overnight, the phases were separated, and the aqueous phase was extracted with CH2Cl2 (3×50 mL). The combined organic phase was dried over anhydrous MgSO4, filtered, and concentrated in vacuo. This crude product was purified by flash chromatography (Combiflash, 0-10% methanol/dichloromethane) to provide (2S)—N,N-dimethyl-1-(phenylcarbonyl)-2-piperidinecarboxamide (883 mg, 74%). LCMS: (M+H)+: not detected.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (3×50 mL)
  3. dry with materialThe combined organic phase was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThis crude product was purified by flash chromatography (Combiflash, 0-10% methanol/dichloromethane)

Sources & evidence

ORD record
ord-843556d66c044483b796040c3d216acd
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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