HCID 59507768, compound → HCID 59507740, compound

HRID 1043799Notes

Reaction equation

HRID 1043799 reaction equation
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-])=O)=[CH:13][C:12]=2OC)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].[H][H]>CO.[OH-].[OH-].[Pd+2]>[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([O:10][C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)[CH2:6][CH2:5]1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 59507768HCID 59507768, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59507740HCID 59507740, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1-isopropyl-4-(2-methoxy-4-nitrophenoxy)piperidine (167 mg, 0.57 mmol) was dissolved in 20 mL of methanol and placed under a nitrogen atmosphere. A catalytic amount of 20% palladium hydroxide on carbon was added and a hydrogen balloon was connected to the reaction flask. The flask was flushed five times with hydrogen and stirred at room temperature under hydrogen atmosphere for 16 hours. The reaction mixture was filtered and washed with methanol. The filtrate was evaporated under reduced pressure. Acetonitrile (1.0 mL) was added to the residue, swirled for 10 min, and decanted away from white film. The acetonitrile layer was evaporated under reduced pressure yielding 4-(1-isopropylpiperidin-4-yloxy)aniline as a brown oil (131 mg, 87%). LC/MS (m/z): 265.2 (MH+), Rt 0.33 minutes.

Workup

  1. customThe flask was flushed five times with hydrogen
  2. filtrationThe reaction mixture was filtered
  3. washwashed with methanol
  4. customThe filtrate was evaporated under reduced pressure
  5. additionAcetonitrile (1.0 mL) was added to the residue
  6. waitswirled for 10 min
  7. customdecanted away from white film
  8. customThe acetonitrile layer was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d30941e27bc748d588f7fc50a8a5599d
Source dataset
uspto-grants-2013_10
Patent number
US08563549B2

Reaction notes

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