HCID 67263902, compound → HCID 67265137, compound

HRID 1041201Notes

Reaction equation

HRID 1041201 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[CH:6]=[CH:5][C:4]=1[N+:20]([O-])=O>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[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH2:13][C:7]=2[CH:6]=[CH:5][C:4]=1[NH2:20]

Participants

4

Reactant 1

HCID 67263902HCID 67263902, compound

Product 1

HCID 67265137HCID 67265137, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The latter nitro isomer, 4-(1-Methoxy-2-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-6-yl)-morpholine (1.51 g, 4.939 mmol) was dissolved in ethanol (100 mL) and hydrogenated over 10% palladium on carbon (151 mg) at 50 psi using a Parr shaker for 3 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 8% methanol: dichloromethane) to afford 1-methoxy-6-morpholin-4-yl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-ylamine (830 mg, 61%) as a brown solid.

Workup

  1. customfor 3 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 8% methanol: dichloromethane)

Sources & evidence

ORD record
ord-f85945fe697d4dd49f083eebe87ce197
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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