Formic acid (ammonium salt) → (S)-2-(4-Phenyl-butyl)-piperazine

HRID 1350392

Reaction equation

HRID 1350392 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][CH:23]=[CH:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)C1C=CC=CC=1.C(O)=O.N>CCO.[Pd]>[C:25]1([CH2:24][CH2:23][CH2:22][CH2:21][C@H:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 10904Formic acid (ammonium salt)HCID 69487542(S)-1,4-Dibenzyl-2-(4-phenyl-but-3-enyl)-piperazine

Product 1

HCID 69487314(S)-2-(4-Phenyl-butyl)-piperazineYield 67.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Combine (S)-1,4-dibenzyl-2-(4-phenyl-but-3-enyl)-piperazine (2.12 g, 5.3 mmol), 10% Pd/C (300 mg, 0.027 mmol) and ammonia formate (1.67 g, 26.5 mmol) in EtOH (50 mL), heat to reflux for 3 hours 30 minutes, and cool to room temperature. Remove the catalyst via filtration, and concentrate the filtrate to a residue. Purification by flash chromatography on silica gel using 2N NH3 in MeOH and dichloromethane (5%–15%) to give the title compound (780 mg, yield 67%): mass spectrum (Electrospray): m/z=219.2 (M+1); 1H NMR (CDCl3): δ7.30–7.15 (m, 5H), 2.96–2.55 (m, 8H), 2.37–2.30 (m, 1H), 1.64–1.60 (m, 2H), 1.39–1.29 (m, 4H).

Workup

  1. temperatureto reflux for 3 hours 30 minutes
  2. customRemove the catalyst
  3. filtrationvia filtration
  4. concentrationconcentrate the filtrate to a residue
  5. customPurification by flash chromatography on silica gel using 2N NH3 in MeOH and dichloromethane (5%–15%)

Sources & evidence

ORD record
ord-e2325a2ae6914fb091d0047178a7cf12
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Linked notes

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