Sodium hydride → 4-(2-Methoxy-ethoxy)-1-(3-methoxy-4-nitro-phenyl)-piperidine

HRID 1366286ノート

反応式

HRID 1366286 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:12]2[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[H-].[Na+].[CH3:21][O:22][CH2:23][CH2:24]Br.[Cl-].[NH4+]>CN(C)C=O.O>[CH3:21][O:22][CH2:23][CH2:24][O:18][CH:15]1[CH2:16][CH2:17][N:12]([C:5]2[CH:6]=[CH:7][C:8]([N+:9]([O-:11])=[O:10])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:14]1

参加物

7

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 809722-Bromoethyl methyl etherHCID 259188601-(3-Methoxy-4-nitrophenyl)piperidin-4-ol

生成物 1

HCID 587485624-(2-Methoxy-ethoxy)-1-(3-methoxy-4-nitro-phenyl)-piperidine収率 29.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(3-Methoxy-4-nitro-phenyl)-piperidin-4-ol (300 mg, 1.2 mmol) in N,N-dimethylformamide (3.0 mL), sodium hydride (1.52 g, 3.8 mmol) is added. After stirring, 2-bromoethyl methyl ether (150 μl, 1.6 mmol) is added and the mixture is further stirred at 70° C. for 15 hours. After addition of saturated aqueous ammonium chloride, the mixture is poured into water and extracted twice with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, and evaporated in vacuo. The residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient) to afford 4-(2-Methoxy-ethoxy)-1-(3-methoxy-4-nitro-phenyl)-piperidine (111 mg, 29%) as a yellow oil.

後処理

  1. stirringthe mixture is further stirred at 70° C. for 15 hours
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue is purified by silica gel column chromatography (n-hexane-ethyl acetate gradient)

出典と根拠

ORDレコード
ord-da1ec44cfdc74f0a9a2264fcd469e448
出典データセット
uspto-grants-2011_02
特許番号
US07893074B2

反応ノート

読み込み中…