Triethylamine → (3,4-Dihydro-2H-benzo[1,4]oxazin-3-yl-methyl)-[3-(5-fluoro-1H-indol-3-yl)propyl]-amine

HRID 427270노트

반응식

HRID 427270 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][CH2:12][CH2:13]OS(C1C=CC(C)=CC=1)(=O)=O.[NH2:25][CH2:26][C:27]1[CH2:28][O:29][C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[N:32]=1.C(N(CC)CC)C>C(#N)C>[O:29]1[C:30]2[CH:36]=[CH:35][CH:34]=[CH:33][C:31]=2[NH:32][CH:27]([CH2:26][NH:25][CH2:13][CH2:12][CH2:11][C:5]2[C:4]3[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=3)[NH:7][CH:6]=2)[CH2:28]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 150205425-Fluoro-3-(3-p-toluenesulfonyloxypropyl)indoleHCID 539412263-Aminomethyl-1,4-benzoxazine

생성물 1

HCID 9945844(3,4-Dihydro-2H-benzo[1,4]oxazin-3-yl-methyl)-[3-(5-fluoro-1H-indol-3-yl)propyl]-amine수율 52.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of 5-fluoro-3-(3-p-toluenesulfonyloxypropyl)indole (0.52 g, 1.5 mmol) and 3-aminomethyl-1,4-benzoxazine (0.25 g, 1.5 mmol) [prepared in accordance with the procedure set forth in Ind. J. Chem., 13:462-467 (1975)] in acetonitrile (15 mL) was added triethylamine (0.42 mL, 3.0 mmol) at room temperature. The reaction mixture was allowed to reflux 18 h, cooled and concentrated. The crude product was purified by silica gel column chromatography (ethyl acetate/methanol/NH4OH, 98/2/0.5) to afford 265 mg (52%) of the free base.

후처리

  1. temperatureto reflux 18 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel column chromatography (ethyl acetate/methanol/NH4OH, 98/2/0.5)

출처 및 근거

ORD 기록
ord-fc7db05ae6904bb39a188413da364d05
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06313114B1

반응 노트

불러오는 중…