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

HRID 1362366ノート

反応式

HRID 1362366 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-460640b88e1d4bb8977386d0a7e38603
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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