Acetyl chloride → 1-{3-[1-(3-Fluorophenyl)methylidene]piperidin-1-yl}ethanone

HRID 928078노트

반응식

HRID 928078 반응식
[C:1](Cl)(=[O:3])[CH3:2].Cl.[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]2[CH2:19][CH2:18][CH2:17][NH:16][CH2:15]2)[CH:10]=[CH:11][CH:12]=1.C(N(C(C)C)CC)(C)C>C1COCC1.O>[F:6][C:7]1[CH:8]=[C:9]([CH:13]=[C:14]2[CH2:19][CH2:18][CH2:17][N:16]([C:1](=[O:3])[CH3:2])[CH2:15]2)[CH:10]=[CH:11][CH:12]=1

참가 물질

6

반응물 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 709838913-[1-(3-Fluorophenyl)methylidene]piperidine hydrochloride2회

생성물 1

HCID 709845881-{3-[1-(3-Fluorophenyl)methylidene]piperidin-1-yl}ethanone

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Acetyl chloride (0.515 mL) was added to a mixture of 3-[1-(3-fluorophenyl)methylidene]-piperidine hydrochloride (Intermediate 226, 1.5 g) and N,N-di-isopropyl-N-ethylamine (2.52 mL) in anhydrous THF (50 mL) at 0° C. under nitrogen. The mixture was allowed to warm to room temperature and was stirred for 2 hours. The mixture was diluted with water (100 mL) and extracted with ether, washed with brine, dried (Na2SO4) and filtered. The filtrate was evaporated to dryness and the residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 75-100% to give 1-{3-[1-(3-fluorophenyl)-methylidene]piperidin-1-yl}ethanone (1.38 g).

후처리

  1. extractionextracted with ether
  2. washwashed with brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness
  6. customthe residue was purified by chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane with a gradient of 75-100%

출처 및 근거

ORD 기록
ord-4354b4a830df48c2854eeaec51d107b0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290472B2

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