Sodium hydride → 1-Acetyl-4-ethynyl-4-(2-nitrophenoxy)piperidine

HRID 1193548

반응식

HRID 1193548 반응식
[Na+].CS([CH2-])=O.[H-].[Na+].[C:8]([N:11]1[CH2:16][CH2:15][C:14]([C:18]#[CH:19])([OH:17])[CH2:13][CH2:12]1)(=[O:10])[CH3:9].F[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[N+:27]([O-:29])=[O:28]>O.CS(C)=O>[C:8]([N:11]1[CH2:16][CH2:15][C:14]([C:18]#[CH:19])([O:17][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[N+:27]([O-:29])=[O:28])[CH2:13][CH2:12]1)(=[O:10])[CH3:9]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 738951-Fluoro-2-nitrobenzeneHCID 10154010Methane, sulfinylbis-, ion(1-), sodiumHCID 132167351-(4-Ethynyl-4-hydroxypiperidin-1-yl)ethan-1-one

생성물 1

HCID 142814881-Acetyl-4-ethynyl-4-(2-nitrophenoxy)piperidine수율 24%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a stirred solution of dimsyl sodium, prepared from 16.5 g of sodium hydride (50% in oil, washed three times with hexanes) and 400 ml of dimethylsulfoxide at 17°-25° was added, in aliquots, 57.7 g of 1-acetyl-4-ethynyl-4-piperidinol. Upon completion of the addition, 55.3 g of 2-fluoronitrobenzene was added dropwise at a rate such that the temperature remained below 25°. The mixture was stirred at room temperature for 20 min, poured into cold water, extracted three times with ether, washed with saturated sodium chloride solution and dried over anhydrous potassium carbonate. Filtration followed by evaporation of solvent provided an oil, which crystallized on standing. Recrystallization from ethyl acetate/cyclohexane provided 23.6 g (24%) of product, mp 112°-115°.

후처리

  1. additionwas added dropwise at a rate such that the temperature
  2. customremained below 25°
  3. extractionextracted three times with ether
  4. washwashed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous potassium carbonate
  6. filtrationFiltration
  7. customfollowed by evaporation of solvent
  8. customprovided an oil, which
  9. customcrystallized
  10. customRecrystallization from ethyl acetate/cyclohexane

출처 및 근거

ORD 기록
ord-3ebe733b3b70488daa38ed37d48b843b
출처 데이터셋
uspto-grants-1989_03
특허 번호
US04810792

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