Formaldehyde → HCID 18176648, compound

HRID 394486Notes

Reaction equation

HRID 394486 reaction equation
[ClH:1].[F:2][C:3]([F:24])([F:23])[C:4]1[CH:5]=[C:6]([CH:20]=[CH:21][CH:22]=1)[O:7][CH2:8][CH2:9][CH2:10][CH2:11][NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C=O.S1C=CC=[CH:28]1.C([O-])(=O)C.[K+].[H][H]>CO.[Pd]>[ClH:1].[CH3:28][N:12]([CH2:11][CH2:10][CH2:9][CH2:8][O:7][C:6]1[CH:20]=[CH:21][CH:22]=[C:4]([C:3]([F:23])([F:24])[F:2])[CH:5]=1)[CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

8

Reactant 5

HCID 712FormaldehydeHCID 8030ThiopheneHCID 517044Potassium AcetateHCID 18176645HCID 18176645, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18176648HCID 18176648, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of intermediate 7 (0.03 mol) and paraformaldehyde (2 g) in methanol (150 ml) was hydrogenated with palladium on carbon (2 g) as a catalyst in the presence of thiophene (4%, 2 ml) and potassium acetate (4 g). After uptake of hydrogen gas (1 equivalent), the catalyst was filtered off and the filtrate was evaporated. The residue was stirred in water and this mixture was extracted with DCM. The separated organic layer was dried, filtered, and the solvent evaporated. The residue was dissolved in DIPE and converted into the hydrochloric acid salt (1:1) with HCl/2-propanol. The precipitate was filtered off and dried, yielding 8.22 g (73%) of N-methyl-N-[4-[3-(trifluoro-methyl)phenoxy]butyl]benzenemethanamine hydrochloride (intermediate 8).

Workup

  1. customthe filtrate was evaporated
  2. extractionthis mixture was extracted with DCM
  3. customThe separated organic layer was dried
  4. filtrationfiltered
  5. customthe solvent evaporated
  6. dissolutionThe residue was dissolved in DIPE
  7. filtrationThe precipitate was filtered off
  8. customdried

Sources & evidence

ORD record
ord-7291af5907aa4dabaa019d7d416784e5
Source dataset
uspto-grants-2003_08
Patent number
US06602873B2

Reaction notes

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