Hydrochloric Acid → HCID 13526574, compound

HRID 638329Notes

Reaction equation

HRID 638329 reaction equation
[C:1]1([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)([CH2:11][CH2:12][N:13]([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C(O)C.[Pt]=O>[C:1]1([C:7]([CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][NH:21]2)([CH2:11][CH2:12][N:13]([CH:14]([CH3:16])[CH3:15])[CH:17]([CH3:18])[CH3:19])[C:8]([NH2:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3114Disopyramide

Product 1

HCID 13526574HCID 13526574, compoundYield 24.3%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 105.3 g (0.31 mole) of racemic 2-phenyl-2-(2-pyridyl)-4-[N,N-bis(1-methylethyl)amino]butanamide and 27 ml (ca. 0.32 mole) of concentrated aqueous hydrochloric acid in 2.5 liters of ethanol was hydrogenated (50 psi) over platinum oxide catalyst. After filtration to remove the catalyst, the reaction mixture was reduced to a syrupy residue, dissolved in an ice/water mixture, and neutralized with a slight excess of 25% sodium hydroxide. The product mixture was extracted into diethyl ether, which was dried over magnesium sulfate, filtered, and concentrated to dryness. The crude product was crystallized twice from Skellysolve B containing a small amount of diethyl ether, to yield 26.0 g of the title compound as a white solid, m.p. 107°-108°. Structure assignment was confirmed by proton and carbon-13 NMR spectra and by elemental analysis.

Workup

  1. filtrationAfter filtration
  2. customto remove the catalyst
  3. dissolutiondissolved in an ice/water mixture
  4. extractionThe product mixture was extracted into diethyl ether, which
  5. dry with materialwas dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe crude product was crystallized twice from Skellysolve B containing a small amount of diethyl ether

Sources & evidence

ORD record
ord-cc3eff44089f40188530b94671fd7f47
Source dataset
uspto-grants-1985_12
Patent number
US04560754

Reaction notes

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