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

HRID 2285906ノート

反応式

HRID 2285906 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e770744589ae4a429c0b658ee622cc96
出典データセット
uspto-grants-1982_04
特許番号
US04325953

反応ノート

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