Ammonium formate → HCID 51970802, compound

HRID 1350404Notes

Reaction equation

HRID 1350404 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][C@@H:9]1[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:32][C:29]([F:30])([F:31])[C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 58860678HCID 58860678, compound

Product 1

HCID 51970802HCID 51970802, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-[2-(4-trifluoromethyl-phenyl)-ethyl]-piperazine (3.34 g, 7.62 mmol), ammonium formate (2.40 g, 38.09 mmol), 5% Pd/C (368.7 mg), and ethanol (100 ml). Stir and heat the mixture at reflux. After 3 hrs, cool to ambient temperature and remove the catalyst by vacuum filtration through celite. Reduce the filtrate to residue and then dissolve it in dichloromethane. Wash the organic with 1N NaOH and then combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue to give 1.83 g (93%) of the title compound as an off-white solid: mp 135°–141°; mass spectrum (ion spray): m/z=259.2 (M+1).

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. customremove the catalyst
  4. filtrationby vacuum filtration through celite
  5. dissolutiondissolve it in dichloromethane
  6. washWash the organic with 1N NaOH
  7. washwash (brine)
  8. dry with materialdry (sodium sulfate)

Sources & evidence

ORD record
ord-bcaa09f936e24f34b111d6525b7dde14
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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