HCID 86699689, compound → HCID 68284027, compound

HRID 1487218Notes

Reaction equation

HRID 1487218 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[CH:7][N:8]2[CH2:13][CH2:14][CH2:15][N:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1)([O-])=O>CO.[Pd]>[O:19]1[CH2:20][CH2:21][N:16]([CH2:15][CH2:14][CH2:13][N:8]2[C:9]3[CH:10]=[CH:11][CH:12]=[C:4]([NH2:1])[C:5]=3[CH:6]=[CH:7]2)[CH2:17][CH2:18]1

Participants

4

Reactant 1

HCID 86699689HCID 86699689, compound

Product 1

HCID 68284027HCID 68284027, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of crude 4-(3-(4-nitro-1H-indol-1-yl)propyl)morpholine in methanol (100 mL) was added palladium on carbon (10%). The mixture was stirred under an atmosphere of hydrogen for 12 hours. The catalyst was removed by filtration and the filtrate was evaporated. The residue was purified by silica gel chromatography to afford the product 1-(3-morpholinopropyl)-1H-indol-4-amine (5 g, yield 67%, two steps) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.12, J=2.4 Hz).

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0dfe562da378487aa0f9b6cce8a8b210
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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