Ammonium formate → (S)-2-(2-(4-Fluoro-phenyl)-ethyl)-piperazine

HRID 1350367Notes

Reaction equation

HRID 1350367 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][C:26]([F:29])=[CH:25][CH:24]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>[Pd].C(O)C>[F:29][C:26]1[CH:27]=[CH:28][C:23]([CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[CH:24][CH:25]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 69486783(S)-1,4-dibenzyl-2-(2-(4-fluoro-phenyl)-ethyl)-piperazine

Product 1

HCID 69487151(S)-2-(2-(4-Fluoro-phenyl)-ethyl)-piperazine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(2-(4-fluoro-phenyl)-ethyl)-piperazine (1.94 g, 4.99 mmol), ammonium formate (1.57 g, 24.95 mmol), 5% Pd/C (241.1 mg), and ethanol (50 mL) and 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 dissolve it in 1N NaOH. Extract with dichloromethane and combine, wash (brine), dry (sodium sulfate), and reduce the extracts to residue. Purify the residue on silica gel using dichloromethane/2N ammonia in methanol (80:20) to give the title compound as a white solid: mp 112–114° 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, 68.97; H, 8.14; N, 13.21.

Workup

  1. temperatureheat the mixture
  2. temperatureat reflux
  3. customremove the catalyst
  4. filtrationby vacuum filtration through celite
  5. dissolutiondissolve it in 1N NaOH
  6. extractionExtract with dichloromethane and combine
  7. washwash (brine)
  8. dry with materialdry (sodium sulfate)
  9. customPurify the residue on silica gel

Sources & evidence

ORD record
ord-336eadae4879461b814ffe56b58956d0
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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