5-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole → 5-methoxy-3-(1-methylpiperidin-4-yl)-1H-indole

HRID 277991ノート

反応式

HRID 277991 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[C:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH:17]=1>C(O)C.O1CCCC1.CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH:12]1[CH2:13][CH2:14][N:15]([CH3:18])[CH2:16][CH2:17]1

参加物

4

反応物 1

HCID 30552495-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole

生成物 1

HCID 113795615-methoxy-3-(1-methylpiperidin-4-yl)-1H-indole収率 97.2%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 66624091Ethanol tetrahydrofuran methanol溶媒

実験手順

5-Methoxy-3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)indole (9.00 g, 37 mmol) was dissolved in 190 mL of ethanol/tetrahydrofuran/methanol (10:10:1). 10% palladium on carbon (2.2 g) was added, and the reaction mixture was hydrogenated at 40 p.s.i. in a Parr shaker for 96 hours. The mixture was filtered through celite, the catalyst was washed with ethanol, and the filtrate was concentrated in vacuo. The residue was chromatographed on silica gel (5-10% 2M ammonia-methanol/dichloromethane) to provide 8.79 g (97%) of the title compound. MS(m/e): 245 (M+). EA calculated for C14H19N3O: C, 68.54; H, 7.81; N, 17.13. Found: C, 68.40; H, 7.52; N, 16.90.

後処理

  1. filtrationThe mixture was filtered through celite
  2. washthe catalyst was washed with ethanol
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was chromatographed on silica gel (5-10% 2M ammonia-methanol/dichloromethane)

出典と根拠

ORDレコード
ord-51bbd5a46bc34511b3c13486cdf4eccd
出典データセット
uspto-grants-2002_03
特許番号
US06358972B1

反応ノート

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