Ammonium formate → (S)-2-Phenethylpiperazine

HRID 1350370Notes

Reaction equation

HRID 1350370 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][CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[CH2:21]([C@H:9]1[CH2:10][NH:11][CH2:12][CH2:13][NH:8]1)[CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69486804(S)-1,4-dibenzyl-2-phenethyl-piperazine

Product 1

HCID 44828673(S)-2-Phenethylpiperazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-phenethyl-piperazine (5.15 g, 13.90 mmol), ammonium formate (4.38 g, 69.49 mmol), 5% Pd/C (672.5 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 by silica gel chromatography using dichloromethane/7N ammonia in methanol (90:10) to give the title compound as a white solid: mp 116–119° C.; mass spectrum (ion spray): m/z=191.2 (M+1); Analysis for C12H18N2: calcd: C, 75.74; H, 9.53; N, 14.72; found: C, 75.90; H, 9.57; N, 14.59.

Workup

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

Sources & evidence

ORD record
ord-986849050ea34d7f98303b978c0cba2d
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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