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

HRID 2097114노트

반응식

HRID 2097114 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-71edb359272c4abe834da01637e39e37
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450307B2

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