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

HRID 1366700노트

반응식

HRID 1366700 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매

실험 절차

(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.

후처리

  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)

출처 및 근거

ORD 기록
ord-843556d66c044483b796040c3d216acd
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893056B2

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