Ammonium formate → HCID 86633674, compound

HRID 1500332Notes

Reaction equation

HRID 1500332 reaction equation
C([O-])=O.[NH4+].C([N:12]1[CH2:17][CH2:16][C:15]([CH2:21][CH2:22][CH2:23][CH3:24])([N:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]1)C1C=CC=CC=1.CO.C(Cl)(Cl)[Cl:28]>CO.[OH-].[OH-].[Pd+2]>[ClH:28].[ClH:28].[CH2:21]([C:15]1([N:18]([CH3:20])[CH3:19])[CH2:16][CH2:17][NH:12][CH2:13][CH2:14]1)[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 2723923Ammonium formateHCID 21584188Chloroform methanolHCID 68408396HCID 68408396, compound

Product 1

HCID 86633674HCID 86633674, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

1.5 g 20% Pd(OH)2/C and 6.95 g (3 eq) ammonium formate were added to a solution of 10 g (1 eq) 1-benzyl-4-butyl-N,N-dimethylpiperidin-4-amine in 100 ml MeOH. The reaction mixture obtained was refluxed for 30 min. The reaction course was monitored by thin-layer chromatography (20% MeOH/CHCl3). Once the conversion was complete, the reaction solution was cooled to room temperature, filtered over celite and rewashed with methanol. The methanol is distilled off, the residue taken up in ethyl acetate/hexane, the solvent decanted off and toluene added. The organic phase thus obtained was concentrated under reduced pressure and the residue taken up in 150 ml dichloromethane. HCl gas was passed through the dichloromethane solution for 20 min, the solvent was distilled off and 7 g (74%) of product were obtained in this way as a white solid.

Workup

  1. customThe reaction mixture obtained
  2. temperaturewas refluxed for 30 min
  3. filtrationfiltered over celite
  4. distillationThe methanol is distilled off
  5. customthe solvent decanted off
  6. additiontoluene added
  7. customThe organic phase thus obtained
  8. concentrationwas concentrated under reduced pressure
  9. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-5f7aa74baff646d58e6b7bdba1e368cc
Source dataset
uspto-grants-2015_12
Patent number
US09206156B2

Reaction notes

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