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

HRID 1350368Notes

Reaction equation

HRID 1350368 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]([F:29])[CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F: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 69486661(S)-1,4-dibenzyl-2-(2-(3-fluoro-phenyl)-ethyl)-piperazine

Product 1

HCID 21093648(S)-2-(2-(3-Fluoro-phenyl)-ethyl)-piperazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(2-(3-fluoro-phenyl)-ethyl)-piperazine (1.96 g, 5.04 mmol), ammonium formate (1.59 g, 25.18 mmol), 5% Pd/C (243.3 mg), and ethanol (50 mL). Stir and heat the mixture at reflux. After 4 hours 30 minutes, 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 the title compound as a white solid: mp 95–99° C.; mass spectrum (ion spray): m/z=209.3 (M+1); Analysis for C12H17FN2: calcd: C, 69.20; H, 8.23; N, 13.45; found: C, 69.13; H, 8.40; N, 13.28.

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-cdc4379d4b894893abfd9ee5750911cf
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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