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Acetyl chloride → 1-(4-Fluorophenethylpiperdin-4-yl]-6-acetamidomethylindoline

HRID 1790449
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HRID 1790449 반응식
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH2:28])[CH:25]=4)[CH2:20][CH2:19]3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1.C(N(CC)CC)C.[OH-].[Na+]>C(#N)C.O>[F:5][C:6]1[CH:30]=[CH:29][C:9]([CH2:10][CH2:11][N:12]2[CH2:13][CH2:14][CH:15]([N:18]3[C:26]4[C:21](=[CH:22][CH:23]=[C:24]([CH2:27][NH:28][C:1](=[O:3])[CH3:2])[CH:25]=4)[CH2:20][CH2:19]3)[CH2:16][CH2:17]2)=[CH:8][CH:7]=1
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참가 물질

7

반응물 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 220380351-[1-(4-Fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline

생성물 1

HCID 100007861-(4-Fluorophenethylpiperdin-4-yl]-6-acetamidomethylindoline수율 54%

시약·촉매·용매 2

HCID 962
Water
용매
HCID 6342Acetonitrile용매

실험 절차

Under ice cooling, acetyl chloride (6.6 ml) was added dropwise into a solution of 1-[1-(4-fluorophenethyl)piperidin-4-yl]-6-aminomethylindoline (30 g) obtained above and triethylamine (9.4 g) in acetonitrile (500 ml) and the resultant mixture was stirred at room temperature for 1 hr. After adding a 5 N aqueous solution (40 ml) of sodium hydroxide and water (500 ml) to the reaction solution, the resulting crystalline precipitates were collected by filtration, washed successively with water and ethyl acetate and then dried at 50° C. overnight to give the crude title compound (22.8 g). This crude product was recrystallized successively from ethyl acetate and ethanol to give the title compound (17.9 g) as white needles (yield: 54%).

후처리

  1. customthe resulting crystalline precipitates
  2. filtrationwere collected by filtration
  3. washwashed successively with water and ethyl acetate
  4. customdried at 50° C. overnight
  5. customto give the crude title compound (22.8 g)
  6. customThis crude product was recrystallized successively from ethyl acetate and ethanol

출처 및 근거

ORD 기록
ord-6456d55eb9c6470e9ebbb30f543165a7
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07071201B2

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