4-Nitrobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester → 4-Aminobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester
Reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][S:18]([C:21]4[CH:26]=[CH:25][C:24]([N+:27]([O-])=O)=[CH:23][CH:22]=4)(=[O:20])=[O:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:4][CH2:3]1>[Pd].C(O)C>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:17][S:18]([C:21]4[CH:22]=[CH:23][C:24]([NH2:27])=[CH:25][CH:26]=4)(=[O:20])=[O:19])[CH:15]=3)[NH:10][CH:9]=2)[CH2:6][CH2:7]1Participants
4
Procedure
A mixture of 4-nitrobenzenesulfonic acid 3-(1-methylpiperidin-4-yl)-1H-indol-5-yl ester (800 mg, 1.92 mmol) and 5% palladium on carbon (230 mg) in ethanol (100 mL) was hydrogenated at atmospheric pressure at ambient temperature for 1 h. The reaction mixture was filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography (silica gel, 10, 11, 12, 15% 2M ammonia in methanol/methylene chloride) to give 580 mg (78%) of homogeneous product as a yellow oil that crystallized upon standing: mp=217-219° C. dec; MS(m/e): 386 (M+1), 384 (M−1); Calculated for C20H23N3O3S: C, 62.32; H, 6.01; N, 10.90. Found: C, 62.30; H, 5.91; N, 10.69.
Workup
- filtrationThe reaction mixture was filtered
- concentrationconcentrated under reduced pressure
- customThe crude product was purified by flash chromatography (silica gel, 10, 11, 12, 15% 2M ammonia in methanol/methylene chloride)
Sources & evidence
- ORD record
- ord-32244612b160484a985adfba1966b37a
- Source dataset
- uspto-grants-2007_06
- Patent number
- US07230011B2
Reaction notes
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