Ammonium formate → HCID 69489570, compound

HRID 1350387Notes

Reaction equation

HRID 1350387 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][CH:26]=[CH:25][C:24]=1[O:29][CH3:30])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69486910HCID 69486910, compound

Product 1

HCID 69489570HCID 69489570, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(2-(2-methoxy-phenyl)-ethyl)-piperazine (2.10 g, 5.24 mmol), ammonium formate (1.65 g, 26.19 mmol), 5% Pd/C (253.6 mg), and ethanol (100 mL). Stir and heat the mixture at reflux. After 3 hours, cool to ambient temperature and remove the catalyst by vacuum filtration through celite. Reduce the filtrate to residue and purify it on silica gel using dichloromethane/2N ammonia in methanol (80:20) to give (1.00 g, 87%) of the title compound: mass spectrum (ion spray): m/z=221.1 (M+1).

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. customremove the catalyst
  4. filtrationby vacuum filtration through celite
  5. custompurify it on silica gel

Sources & evidence

ORD record
ord-9ba87d46da404182846e0416e942cedc
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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