Potassium Carbonate → tert-Butyl{1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]piperidin-4-yl}carbamate

HRID 1644407노트

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HRID 1644407 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:22]/[CH:23]=[CH:24]/[C:25]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=1[F:32]>C(O)C>[C:10]([O:9][C:8](=[O:14])[NH:7][CH:4]1[CH2:3][CH2:2][N:1]([CH2:22]/[CH:23]=[CH:24]/[C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH2:6][CH2:5]1)([CH3:11])([CH3:13])[CH3:12]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 7238334-(N-Boc-amino)piperidineHCID 11608064(E)-2-(3-Chloroprop-1-en-1-yl)-1,4-difluorobenzene2회

생성물 1

HCID 86642637tert-Butyl{1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]piperidin-4-yl}carbamate수율 70.9%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
80 °C

실험 절차

A mixture of tert-butyl piperidin-4-ylcarbamate (248 mg, 1.2 mmol), potassium carbonate (188 mg, 1.4 mmol) and 2-[(1E)-3-chloroprop-1-en-1-yl]-1,4-difluorobenzene (Intermediate 124, 257 mg, 1.4 mmol) in ethanol (7 mL) was heated to 80° C. for 18 hours. The mixture was concentrated under reduced pressure, the residue taken up in dichloromethane (20 mL) and water (20 mL), the aqueous phase was back extracted with dichloromethane (2×20 mL) and the combined organic phases were dried over sodium sulfate. Chromatography on silica gel with dichloromethane/methanol (95:5) gave 300 mg (69%) of product as a brown foam.

후처리

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionwater (20 mL), the aqueous phase was back extracted with dichloromethane (2×20 mL)
  3. dry with materialthe combined organic phases were dried over sodium sulfate

출처 및 근거

ORD 기록
ord-3429e9fe41e04ecb860dd11907b92135
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124602B2

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