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

HRID 427270ノート

反応式

HRID 427270 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-fc7db05ae6904bb39a188413da364d05
出典データセット
uspto-grants-2001_11
特許番号
US06313114B1

反応ノート

読み込み中…