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

HRID 1350369Notes

Reaction equation

HRID 1350369 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[F:29])C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F: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 69486865(S)-1,4-dibenzyl-2-(2-(2-fluoro-phenyl)-ethyl)-piperazine

Product 1

HCID 69489569(S)-2-(2-(2-Fluoro-phenyl)-ethyl)-piperazineYield 78.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(2-(2-fluoro-phenyl)-ethyl)-piperazine (1.06 g, 2.73 mmol), ammonium formate (861.0 mg, 13.66 mmol), 5% Pd/C (132.0 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 (443.8 mg, 78%) of the title compound as a white solid: mp 94–99° 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, 69.20; H, 8.26; N, 13.57.

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-0be2d1f94f064ef3bb74f4cffbbfa3f1
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

Loading…