1-Acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo [2,3-f]indole → 1-Acetyl-7-(1-methylpiperidin-4-yl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole
Reaction equation
[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[C:11]([C:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH:17]=4)=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]>[Pd].CO.CN(C=O)C.C(O)(=O)C>[C:1]([N:4]1[C:8]2=[CH:9][C:10]3[C:11]([CH:16]4[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]4)=[CH:12][NH:13][C:14]=3[CH:15]=[C:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]Participants
6
Reactant 1
Product 1
Reagents, catalysts & solvents 4
Procedure
A mixture of 1-acetyl-7-(1-methyl-1,2,5,6-tetrahydropyridin-4-yl)-1,2,3,5-tetrahydropyrrolo[2,3-f]indole (D4, 1.10 g, 3.7 mmole), 10% palladium on carbon (0.20 g) in MeOH (50 ml), DMF (10 ml) and glacial acetic acid (0.5 ml) was shaken under hydrogen at 50 psi/344.8 kPa for 42 hours. The mixture was filtered through Celite (Diatomaceous Earth) and the filtrate evaporated to dryness. The residue was dissolved in water (10 ml) and the pH adjusted to 8 with solid potassium carbonate. The precipitate was collected by filtration washed with water and dried in vacuo to leave the title compound as a buff powder (0.60 g).
Workup
- filtrationThe mixture was filtered through Celite (Diatomaceous Earth)
- customthe filtrate evaporated to dryness
- dissolutionThe residue was dissolved in water (10 ml)
- filtrationThe precipitate was collected by filtration
- washwashed with water
- customdried in vacuo
Sources & evidence
- ORD record
- ord-927204d0f0af4b5ba7f59af28c7918dc
- Source dataset
- uspto-grants-2002_05
- Patent number
- US06391891B1
Reaction notes
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