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

HRID 635386Notes

Reaction equation

HRID 635386 reaction equation
[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]

Participants

4

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ee6daca5bc9c4f72aee5ea56ef00dad8
Source dataset
uspto-grants-2001_02
Patent number
US06187805B1

Reaction notes

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