Potassium Carbonate → (S)-1-(4'-Chloro-biphenyl-2-ylmethyl)-2-methyl-piperidin-4-one

HRID 2406230노트

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HRID 2406230 반응식
Cl.[CH3:2][C@H:3]1[CH2:8][C:7](=[O:9])[CH2:6][CH2:5][NH:4]1.C([O-])([O-])=O.[K+].[K+].[Cl:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29]I)=[CH:19][CH:18]=1>C(#N)C>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[CH2:29][N:4]2[CH2:5][CH2:6][C:7](=[O:9])[CH2:8][C@@H:3]2[CH3:2])=[CH:21][CH:22]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 670542934'-Chloro-2-(iodomethyl)biphenylHCID 67980815(S)-2-Methylpiperidin-4-one hydrochloride

생성물 1

HCID 67980706(S)-1-(4'-Chloro-biphenyl-2-ylmethyl)-2-methyl-piperidin-4-one수율 85%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

(S)-2-Methyl-piperidin-4-one hydrochloride (100 mg, 0.67 mmol) was combined with K2CO3 (554 mg, 4.0 mmol) in acetonitrile (5.0 mL) and stirred for 15 minutes. 4′-Chloro-2-(iodomethyl)biphenyl (220 mg, 0.668 mmol) was added, and the resulting mixture was heated to 70° C. and stirred for 16 hours. The reaction was cooled to room temperature, filtered, and concentrated. The crude residue was purified by flash chromatography on silica gel (heptanes/EtOAc gradient) to afford the title compound as an off-white solid (178 mg, 85% yield). MS (ESI) m/e (M+H+): 313.8

후처리

  1. stirringstirred for 16 hours
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude residue was purified by flash chromatography on silica gel (heptanes/EtOAc gradient)

출처 및 근거

ORD 기록
ord-2b5c3c16db384efd89302892ba4eec9a
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809352B2

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