Methyl iodide → 4-Methoxy-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

HRID 1384016ノート

反応式

HRID 1384016 の反応式
[OH:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=3)[N:7]([CH2:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:38]I>CN(C)C=O>[CH3:38][O:1][C:2]1[C:10]2[N:9]=[C:8]([CH2:11][O:12][C:13]3[CH:14]=[CH:15][C:16]([Cl:19])=[CH:17][CH:18]=3)[N:7]([CH2:20][CH2:21][CH2:22][CH:23]3[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]3)[C:6]=2[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 211887714-Hydroxy-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole

生成物 1

HCID 211887024-Methoxy-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole収率 50%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A solution of 4-hydroxy-2-[(4-chlorophenoxy)methyl]-1-[3-[1-(t-butoxycarbonyl)piperidin-4-yl]propyl]benzimidazole (300 mg, 0.6 mmol, 1 eq) in anhydrous N,N-dimethylformamide (3 m) was treated with sodium hydride (60% in mineral oil, 26 mg, 0.66 mmol, 1.1 eq). The resulting mixture was stirred for thirty minutes at room temperature. Methyl iodide (94 mg, 0.66 mmol, 1 eq) was added to the reaction and the resulting mixture was stirred for two hours at room temperature. The reaction was quenched with the addition of water (5 ml). The aqueous fraction was extracted with ethyl acetate (3×10 ml). The organic fractions were combined, washed with water (2×10 ml), then brine (1×10 ml), and then dried over sodium sulfate. The solvents were removed in vacuo. The residue was further purified by flash column chromatography to yield the title product as a crystalline product in 50% yield.

後処理

  1. stirringthe resulting mixture was stirred for two hours at room temperature
  2. customThe reaction was quenched with the addition of water (5 ml)
  3. extractionThe aqueous fraction was extracted with ethyl acetate (3×10 ml)
  4. washwashed with water (2×10 ml)
  5. dry with materialbrine (1×10 ml), and then dried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customThe residue was further purified by flash column chromatography

出典と根拠

ORDレコード
ord-ab7203fe7278483c9e80ace08f0614d6
出典データセット
uspto-grants-2001_07
特許番号
US06255494B1

反応ノート

読み込み中…