4-(3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)morpholine → 2-(2-Fluorophenyl)-2-(6-morpholino-1H-indol-3-yl)ethanamine

HRID 2361238Notes

Reaction equation

HRID 2361238 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:9][N+:10]([O-])=O.[H][H]>CO.[Ni]>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([C:13]1[C:21]2[C:16](=[CH:17][C:18]([N:22]3[CH2:23][CH2:24][O:25][CH2:26][CH2:27]3)=[CH:19][CH:20]=2)[NH:15][CH:14]=1)[CH2:9][NH2:10]

Participants

5

Reactant 2

HCID 679949054-(3-(1-(2-Fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)morpholineHCID 178418361HCID 178418361, compound

Product 1

HCID 679947912-(2-Fluorophenyl)-2-(6-morpholino-1H-indol-3-yl)ethanamineYield 84%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(3-(1-(2-fluorophenyl)-2-nitroethyl)-1H-indol-6-yl)morpholine (0.235 g, 0.636 mmol) and Raney Ni (a small spatula) in MeOH (30 mL) was treated with hydrogen at 55 psi in a Parr shaker apparatus for 3 hr. The catalyst was removed by suction filtration. The filtrate was concentrated under vacuum, diluted with CH2Cl2 (100 mL), washed with brine (25 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.181 g, 0.533 mmol, 84% yield) as an off-white solid.

Workup

  1. customThe catalyst was removed by suction filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. additiondiluted with CH2Cl2 (100 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-e2dc87c02179445f8bf313f88df01143
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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