N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine → 1-Benzenesulfonyl-3-(2-dimethylamino-ethyl)-1H-indol-5-ol

HRID 635386노트

반응식

HRID 635386 반응식
[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15]CC3C=CC=CC=3)[CH:13]=2)[N:8]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:25])=[O:24])[CH:7]=1)[CH3:3]>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:1][N:2]([CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:15])[CH:13]=2)[N:8]([S:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)(=[O:24])=[O:25])[CH:7]=1)[CH3:3]

참가 물질

4

반응물 1

HCID 11729763N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine

생성물 1

HCID 98410771-Benzenesulfonyl-3-(2-dimethylamino-ethyl)-1H-indol-5-ol

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 702Ethanol용매

실험 절차

A solution of N,N-dimethyl 2-(1-benzenesulphonyl-5-benzyloxy-1H-indol-3-yl)ethylamine (2.25 g, 4.6 mmol) in absolute ethanol (100 ml) was hydrogenated at 40 psi over 20% palladium hydroxide (600 mg) for 4.5 h. Additional catalyst (1.6 g) was then added and hydrogenation was resumed at 45 psi for 2.5 h. The catalyst was removed by filtration, washed with a mixture of dichloromethane-methanol-ammonia (80:20:2; 3×70 ml), and the filtrate was concentrated under vacuum. The residue was purified by flash chromatography (silica gel, dichloromethane-methanol-ammonia, 95:5:0.5) to give the title compound as a crystalline solid after trituration with diethyl ether (30 ml); mp 185°-188° C.; δH (360 MHz, DMSO-d6) 9.32 (1H, br s), 7.90-7.84 (2H, m), 7.69 (1H, d, J=8.7 Hz), 7.68-7.62 (1H, m), 7.55 (2H, t, J=8.0 Hz), 7.48 (1H, s), 6.82 (1H, d, J=2.2 Hz), 6.78 (1H, dd, H=8.8 and 2.2 Hz), 2.67 (2H, t, J=7.6 Hz), 2.47 (2H, t, J=7.6 Hz), 2.18 (6H, s); m/z (ES) 345 (M++1). (Found: C, 62.91; H, 5.86; N, 8.16. C18H20N2O3 requires: C, 62.77; H, 5.85; N, 8.13%).

후처리

  1. customThe catalyst was removed by filtration
  2. washwashed with a mixture of dichloromethane-methanol-ammonia (80:20:2; 3×70 ml)
  3. concentrationthe filtrate was concentrated under vacuum
  4. customThe residue was purified by flash chromatography (silica gel, dichloromethane-methanol-ammonia, 95:5:0.5)

출처 및 근거

ORD 기록
ord-ee6daca5bc9c4f72aee5ea56ef00dad8
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06187805B1

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