Ammonium formate → (S)-2-(Piperazin-2-yl)ethanol

HRID 131397Notes

Reaction equation

HRID 131397 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][OH:23])C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[NH:8]1[CH2:13][CH2:12][NH:11][CH2:10][C@@H:9]1[CH2:21][CH2:22][OH:23]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 59732113(S)-2-(1,4-Dibenzylpiperazin-2-yl)ethanol

Product 1

HCID 1519380(S)-2-(Piperazin-2-yl)ethanolYield 101.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

Dissolve (S)-2-(1,4-dibenzylpiperazin-2-yl)ethanol (11.7 g, 0.038 mol) in 380 mL of ethanol, add 10% palladium on carbon (3.7 g of wet reagent, 50% by weight) as a suspension in a few mL of ethanol. Add excess ammonium formate (16.8 g, 0.27 mol) all at once. Heat at reflux for 5 h, cool to room temperature and filter through a celite pad, washing well with ethanol. Concentrate filtrate in vacuo to provide the title compound (5 g, quantitative) as a cloudy residue. Use directly on the next step without further purification: mass spectrum (APCI): m/z=131.1 (M+1).

Workup

  1. temperatureHeat
  2. temperatureat reflux for 5 h
  3. filtrationfilter through a celite pad
  4. washwashing well with ethanol

Sources & evidence

ORD record
ord-a15daf12e9904e39b388239e81d0bfe3
Source dataset
uspto-grants-2008_06
Patent number
US07384934B2

Reaction notes

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