HCID 67264121, compound → HCID 67264662, compound

HRID 1687507Notes

Reaction equation

HRID 1687507 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH2:11][CH:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:13][C:7]=2[C:6]([N+:20]([O-])=O)=[CH:5][CH:4]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH2:11][CH:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[CH2:13][C:7]=2[C:6]([NH2:20])=[CH:5][CH:4]=1

Participants

4

Reactant 1

HCID 67264121HCID 67264121, compound

Product 1

HCID 67264662HCID 67264662, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-(1-Methoxy-4-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-morpholine (1.51 g, 4.94 mmol) was dissolved in ethanol (100 mL) and hydrogenated over 10% palladium on carbon (151 mg) at 50 psi using a Parr shaker for 4 hours. The palladium was removed by filtration and the ethanol was concentrated to afford a brown foam which was purified via ISCO chromatography (gradient elution: 2 to 10% methanol:dichloromethane) to afford 4-methoxy-8-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-1-ylamine (1.37 g, 99%) as a light brown solid.

Workup

  1. customfor 4 hours
  2. customThe palladium was removed by filtration
  3. concentrationthe ethanol was concentrated
  4. customto afford a brown foam which
  5. customwas purified via ISCO chromatography (gradient elution: 2 to 10% methanol:dichloromethane)

Sources & evidence

ORD record
ord-3ecb721724964f358d3b3bb4ab457c18
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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