Methylamine → (3-Chloro-benzofuran-2-ylmethyl)methylamine

HRID 2097114ノート

反応式

HRID 2097114 の反応式
[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH:11]=O.[CH3:13][NH2:14].[BH4-].[Na+]>CO>[Cl:1][C:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][C:3]=1[CH2:11][NH:14][CH3:13]

参加物

5

反応物 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 47370203-Chlorobenzofuran-2-carboxaldehyde

生成物 1

HCID 59277587(3-Chloro-benzofuran-2-ylmethyl)methylamine収率 82.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 3-chlorobenzofuran-2-carboxaldehyde (1.62 g, 8.9 mmol) in methanol (50 mL) is added N-methylamine (33% solution in ethanol, 1.11 g, 35.9 mmol) and stirred overnight at room temperature. The mixture is concentrated in vacuo, re-solvated in methanol (50 mL) and cooled in an ice bath. Sodium borohydride (407 mg, 10.8 mmol) is added in portions and the mixture stirred at room temperature for 4 h. The mixture is concentrated in vacuo, re-solvated in 1.3M sodium hydroxide solution, stirred for 20 min, extracted with ethyl acetate, dried with sodium sulfate and concentrated. Purification by column chromatography (silica, CH2Cl2/MeOH, 9/1) gave title compound (1.43 g, 82%) as a colorless oil. 1H NMR (300 MHz, DMSO-d6) δ 7.55-7.63 (m, 2H), 7.33-7.42 (m, 2H), 3.93 (s, 2H), 2.27 (s, 3H).

後処理

  1. concentrationThe mixture is concentrated in vacuo, re-solvated in methanol (50 mL)
  2. temperaturecooled in an ice bath
  3. stirringthe mixture stirred at room temperature for 4 h
  4. concentrationThe mixture is concentrated in vacuo, re-solvated in 1.3M sodium hydroxide solution
  5. stirringstirred for 20 min
  6. extractionextracted with ethyl acetate
  7. dry with materialdried with sodium sulfate
  8. concentrationconcentrated
  9. customPurification by column chromatography (silica, CH2Cl2/MeOH, 9/1)

出典と根拠

ORDレコード
ord-71edb359272c4abe834da01637e39e37
出典データセット
uspto-grants-2013_05
特許番号
US08450307B2

反応ノート

読み込み中…