Acetaldehyde, 2,2-dimethoxy- → HCID 58168570, compound

HRID 446419Notes

Reaction equation

HRID 446419 reaction equation
Cl.[F:2][C:3]([F:8])([F:7])[CH2:4][CH2:5][NH2:6].[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH:12]=O.C(=O)(O)[O-].[Na+]>CO.[Pd]>[CH3:9][O:10][CH:11]([O:14][CH3:15])[CH2:12][NH:6][CH2:5][CH2:4][C:3]([F:8])([F:7])[F:2]

Participants

6

Reactant 3

HCID 162650Acetaldehyde, 2,2-dimethoxy-HCID 516892Sodium BicarbonateHCID 252105053,3,3-Trifluoropropylamine hydrochloride

Product 1

HCID 58168570HCID 58168570, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

To a stirred solution of 3,3,3-trifluoropropan-1-amine hydrochloride (0.165 g) in methanol (3 mL) was added 2,2-dimethoxyacetaldehyde (60% in water, 0.17 mL) followed by sodium bicarbonate (0.093 g) and the mixture was stirred at ambient temperature overnight. A slurry of palladium on carbon 10% (50 mg) in methanol (1 mL) was added and the mixture was hydrogenated at 5 bar pressure for 4 hours. The mixture was filtered and concentrated in vacuo. The resulting gummy solid was suspended in DCM (5 mL) and dried over sodium sulphate, filtered and evaporated to give the titled compound as a yellow gum. Yield 0.152 g.

Workup

  1. waitthe mixture was hydrogenated at 5 bar pressure for 4 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated in vacuo
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-153f134d60544408946a1e09166d8479
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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