Formaldehyde → HCID 68465411, compound

HRID 503002Notes

Reaction equation

HRID 503002 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:22])[C:10]([C:13]([NH:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)([CH3:15])[CH3:14])=[N:11][N:12]=1.C=O.[C:25](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(#N)C>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]([CH3:22])[C:10]([C:13]([N:16]([CH3:25])[CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)([CH3:15])[CH3:14])=[N:11][N:12]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68469024HCID 68469024, compound

Product 1

HCID 68465411HCID 68465411, compoundYield 286.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To an acetonitrile (10 ml) solution of N-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}cyclopentanamine (120 mg) were added 36% formaldehyde solution (92 μl) and sodium triacetoxyborohydride (239 mg), followed by stirring at room temperature for 6 hours. After chloroform, a 1M aqueous sodium hydroxide solution, and distilled water were added to the reaction solution, the organic layer was separated. Furthermore, the organic layer washed with a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and filtered and then the solvent was removed by evaporation under reduced pressure. The resulting crude product was purified by flash column chromatography (chloroform:methanol=25:1). 4M hydrogen chloride-ethyl acetate (0.38 ml) was added to an ethyl acetate (15 ml) solution of the resulting product and, after stirring at room temperature for 30 minutes, the precipitated solid was collected by filtration to obtain 146 mg of N-{1-[5-(2-chlorophenyl)-4-methyl-4H-1,2,4-triazol-3-yl]-1-methylethyl}-N-methylcyclopentanamine dihydrochloride (colorless solid).

Workup

  1. distillationAfter chloroform, a 1M aqueous sodium hydroxide solution, and distilled water
  2. additionwere added to the reaction solution
  3. customthe organic layer was separated
  4. washFurthermore, the organic layer washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed by evaporation under reduced pressure
  8. customThe resulting crude product was purified by flash column chromatography (chloroform:methanol=25:1)
  9. addition4M hydrogen chloride-ethyl acetate (0.38 ml) was added to an ethyl acetate (15 ml) solution of the resulting product
  10. stirringafter stirring at room temperature for 30 minutes
  11. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-c35acb6ebb5644f4a52c0d62abe5568d
Source dataset
uspto-grants-2010_08
Patent number
US07776897B2

Reaction notes

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