Ammonium formate → (S)-1-Phenyl-2-piperazin-2-yl-ethanol

HRID 1350526Notes

Reaction equation

HRID 1350526 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH:9]1[CH2:21][C@@H:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[OH:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[OH-].[Pd+2].[OH-]>[NH3:8].[C:24]1([C@@H:22]([OH:23])[CH2:21][CH:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 69489665(S)-2-(1,4-Dibenzyl-piperazin-2-yl)-1-phenyl-ethanol

Product 2

HCID 222AmmoniaHCID 69489678(S)-1-Phenyl-2-piperazin-2-yl-ethanolYield 82.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent2×

Procedure

Dissolve (S)-2-(1,4-dibenzyl-piperazin-2-yl)-1-phenyl-ethanol (3.89 g, 10.1 mmol) in ethanol (50 mL). Add ammonium formate (3.8 g, 60.4 mmol), palladium hydroxide (1.6 g, 20 wt. % on carbon) and ethanol (25 mL). Heat to reflux. After 6.5 h, cool and stir at ambient temperature 18 h. Filter the palladium hydroxide and concentrate the filtrate. Purify by silica gel chromatography using 2N ammonia in methanol-methylene chloride (10%) then 7N ammonia in methanol-methylene chloride (10%) as the eluent to give 860 mg (41%) of the title compound: mass spectrum (ion spray): m/z=207 (M+1).

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. filtrationFilter the palladium hydroxide
  4. concentrationconcentrate the filtrate
  5. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-13b63a2e55d948c69116a346a3280567
Source dataset
uspto-grants-2007_05
Patent number
US07214673B2

Reaction notes

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