Ammonium formate → (S)-2-(2-(3-Methoxy-phenyl)-ethyl)-piperazine

HRID 1350386Notes

Reaction equation

HRID 1350386 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]=[C:25]([O:29][CH3:30])[CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH3:30][O:29][C:25]1[CH:24]=[C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 17759585(S)-1,4-Dibenzyl-2-(2-(3-methoxy-phenyl)-ethyl)-piperazine

Product 1

HCID 17759586(S)-2-(2-(3-Methoxy-phenyl)-ethyl)-piperazineYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(2-(3-methoxy-phenyl)-ethyl)-piperazine (2.15 g, 5.37 mmol), ammonium formate (1.69 g, 26.84 mmol), 5% Pd/C (259.7 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/7N ammonia in methanol (90:10) to give (1.11 g, 94%) of the title compound as a white solid: mp 53–57° C.; mass spectrum (ion spray): m/z=221.1 (M+1); Analysis for C13H20N2O: calcd: C, 70.87; H, 9.15; N, 12.72; found: C, 70.52; H, 9.06; N, 12.74.

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-c37acb2bc3ed4c29974fd09b0c780596
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…