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4-Bromophenetole → 2-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid

HRID 409732
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인쇄 미리보기

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HRID 409732 반응식
C[O:2][C:3](=[O:18])[CH:4]([C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH3:5].Br[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][CH:21]=1.C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C>O1CCOCC1>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([N:15]2[CH2:16][CH2:17][CH:12]([C:9]3[CH:10]=[CH:11][C:6]([CH:4]([CH3:5])[C:3]([OH:2])=[O:18])=[CH:7][CH:8]=3)[CH2:13][CH2:14]2)=[CH:21][CH:22]=1)[CH3:28]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 685234-BromophenetoleHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 866861172-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester

생성물 1

HCID 866861212-{4-[1-(4-Ethoxy-phenyl)-piperidin-4-yl]-phenyl}-propionic acid

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

1.00 g (4.04 mmol) 2-(4-Piperidin-4-yl-phenyl)-propionic acid methyl ester (XI.3) are added to a mixture of 813 mg (4.04 mmol) 1-bromo-4-ethoxy-benzene, 1.60 g (97%, 16.2 mmol) sodium tert-butyrat, 483 mg (1.62 mmol) 2-(di-tert-butylphosphino)biphenyl and 370 mg (0.40 mmol) tris-(dibenzylidenaceton)-dipalladium(0) in 10 mL 1,4-dioxane. The mixture is stirred for 12 h at 70° C. After that time, the precipitate is filtered off and washed with ACN and diethyl ether. The residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH) to yield the desired product.

후처리

  1. filtrationAfter that time, the precipitate is filtered off
  2. washwashed with ACN and diethyl ether
  3. customThe residue is purified by HPLC (column: Waters XBridge 50; eluent A: water+0.3% NH4OH, eluent B: MeOH)

출처 및 근거

ORD 기록
ord-231ffbaf321c48d4b9ccb408ca3d3bcf
출처 데이터셋
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08759528B2

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