Ammonium formate → HCID 54468976, compound

HRID 1977910Notes

Reaction equation

HRID 1977910 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[N:25]=[C:24]([C:26]4[CH:30]=[C:29]([CH3:31])[NH:28][C:27]=4[CH3:32])[CH:23]=[CH:22][CH:21]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:32][C:27]1[NH:28][C:29]([CH3:31])=[CH:30][C:26]=1[C:24]1[CH:23]=[CH:22][CH:21]=[C:20]([C:17]2[CH:18]=[CH:19][C:14]([CH:11]3[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)=[CH:15][CH:16]=2)[N:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 53826978HCID 53826978, compound

Product 1

HCID 54468976HCID 54468976, compoundYield 77.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 702EthanolSolvent

Procedure

To a 100 mL round-bottomed flask equipped with condenser and N2 inlet were added 1.21 g (2.87 mmol) N-benzyl-4-(4-(2-(2,5-dimethylpyrrolyl)pyrid-6-yl)phenyl)piperidine, 30 mL ethanol, 0.90 g (14.37 mmol) ammonium formate, and 140 mg 10% palladium-on-carbon (Pd-C). The reaction was refluxed 1 hour treated with additional ammonium formate and Pd-C, and refluxed 3 hours. It was then cooled and filtered through Celite with ethanol and methylene chloride. The filtrate was evaporated, taken up in ethyl acetate and aqueous sodium bicarbonate solution, and the organic layer separated, washed with brine, dried over sodium sulfate, and evaporated to afford 734 mg (77%) of an oil.

Workup

  1. customTo a 100 mL round-bottomed flask equipped with condenser and N2 inlet
  2. temperatureThe reaction was refluxed 1 hour
  3. temperaturerefluxed 3 hours
  4. temperatureIt was then cooled
  5. filtrationfiltered through Celite with ethanol and methylene chloride
  6. customThe filtrate was evaporated
  7. customaqueous sodium bicarbonate solution, and the organic layer separated
  8. washwashed with brine
  9. dry with materialdried over sodium sulfate
  10. customevaporated

Sources & evidence

ORD record
ord-079d0750ad4a4a28b3bc9d44cabc3005
Source dataset
uspto-grants-2001_05
Patent number
US06235750B1

Reaction notes

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