Water → 2-(1-Methyl-4-phenyl-4-piperidinyloxy)pyridine

HRID 2285906노트

반응식

HRID 2285906 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([OH:8])[CH2:4][CH2:3]1.[H-].[Na+].F[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.O>CS(C)=O>[CH3:1][N:2]1[CH2:7][CH2:6][C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)([O:8][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=2)[CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 962WaterHCID 97462-FluoropyridineHCID 24758Sodium hydrideHCID 786701-Methyl-4-phenylpiperidin-4-ol

생성물 1

HCID 205426042-(1-Methyl-4-phenyl-4-piperidinyloxy)pyridine수율 37.3%

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매

실험 절차

A solution of 1-methyl-4-phenyl-4-piperidinol (prepared by reaction of 1-methyl-4-piperidone with phenyl lithium; 3.83 g, 20 mM) in dry DMSO (50 ml) was treated with sodium hydride (960 mg of 50% dispersion in oil, 20 mM), stirred for 1 hour then treated with 2-fluoro-pyridine (1.94 g, 20 mM). After 48 hours the reaction was poured on to water (200 ml) and extracted with ether (3×200 ml). The organic extract was washed with brine, dried and the solvent removed under reduced pressure. Recrystallisation of the residue from cyclohexane gave the title compound (2.0 g,) m.p. 95°-6° C.

후처리

  1. extractionextracted with ether (3×200 ml)
  2. extractionThe organic extract
  3. washwas washed with brine
  4. customdried
  5. customthe solvent removed under reduced pressure
  6. customRecrystallisation of the residue from cyclohexane

출처 및 근거

ORD 기록
ord-e770744589ae4a429c0b658ee622cc96
출처 데이터셋
uspto-grants-1982_04
특허 번호
US04325953

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