Methylamine hydrochloride → 3-(5-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide

HRID 1716658노트

반응식

HRID 1716658 반응식
[CH3:1][NH2:2].Cl.C[Al](C)C.C(O[C:11](=[O:31])[CH2:12][CH:13]([C:20]1[C:28]([O:29][CH3:30])=[CH:27][CH:26]=[C:25]2[C:21]=1[CH:22]=[CH:23][NH:24]2)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)C>C1C=CC=CC=1>[CH3:30][O:29][C:28]1[C:20]([CH:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:12][C:11]([NH:2][CH3:1])=[O:31])=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2

참가 물질

5

반응물 3

HCID 6364545Methylamine hydrochlorideHCID 16682925TrimethylaluminumHCID 598318913-(5-Methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester

생성물 1

HCID 598319013-(5-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

To a 0° C. suspension of MeNH2—HCl (15.6 mg, 0.231 mmol) in benzene (2 ml) was added Me3Al (2M in toluene, 115 μl, 2.31 mmol). The mixture was stirred at 0° C. for 5 min and at RT for 2 hours after which a solution of 3-(5-methoxy-1H-Indol-4-yl)-3-phenyl-propionic acid ethyl ester XLIX in benzene (4 ml) was added. The reaction mixture was stirred at reflux for 5 hours and at room temperature for 16 hours, and quenched by addition of HCl (0.5 M). The aqueous layer was extracted with EtOAc. The organic layers were combined, dried over Na2SO4, filtered, and concentrated to yield crude 3-(5-Methoxy-1H-Indol-4-yl)-N-methyl-3-phenyl-propionamide L (37 mg, yellow oil), which was used without purification in the next step.

후처리

  1. additionwas added
  2. customquenched by addition of HCl (0.5 M)
  3. extractionThe aqueous layer was extracted with EtOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-908fc0f2ef2347f0ae62350bd06dc108
출처 데이터셋
uspto-grants-2010_09
특허 번호
US07803830B2

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