HCID 23497787, compound → HCID 191331, compound

HRID 1837149Notes

Reaction equation

HRID 1837149 reaction equation
[CH2:1]([N:3]([CH2:17][CH3:18])[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=O)[CH3:2]>C(O)(=O)C.[Pd]>[CH2:1]([N:3]([CH2:4][CH2:5][CH2:6][C:8]1[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=1)[CH2:17][CH3:18])[CH3:2]

Participants

4

Reactant 1

HCID 23497787HCID 23497787, compound

Product 1

HCID 191331HCID 191331, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

A slurry of 5% Pd/C (2.5 g) in glacial acetic acid (30 mL) was added to a solution of 3-(diethylamino)-4′-nitro-propiophenone (14.33 g, 50 mmol) in glacial acetic acid (150 mL). The mixture was shaken on a Parr shaker under hydrogen pressure for about 20 hours. The catalyst was filtered, and the solvent was evaporated to dryness. The resulting amber liquid was dissolved in ether and washed twice with 2N NaOH (150 mL). The ether layer was dried and evaporated to give N,N-diethyl-3-(p-nitrophenyl)-propylamine as an oil.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent was evaporated to dryness
  3. dissolutionThe resulting amber liquid was dissolved in ether
  4. washwashed twice with 2N NaOH (150 mL)
  5. dry with materialThe ether layer was dried
  6. customevaporated

Sources & evidence

ORD record
ord-22a8150a56db410f88bb91bc4fe15fb8
Source dataset
uspto-grants-2004_08
Patent number
US06780883B2

Reaction notes

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