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

HRID 1366700ノート

反応式

HRID 1366700 の反応式
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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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)

出典と根拠

ORDレコード
ord-843556d66c044483b796040c3d216acd
出典データセット
uspto-grants-2011_02
特許番号
US07893056B2

反応ノート

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