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

HRID 277991노트

반응식

HRID 277991 반응식
[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

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 66624091Ethanol tetrahydrofuran methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-51bbd5a46bc34511b3c13486cdf4eccd
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06358972B1

반응 노트

불러오는 중…