Hydrochloric Acid → 2-(1'-Pyrrolidinocarbonyloxymethyl)piperazine hydrochloride

HRID 1860442Notes

Reaction equation

HRID 1860442 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11](CC2C=CC=CC=2)[CH2:10][CH:9]1[CH2:21][O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1)=[O:24])C1C=CC=CC=1.[ClH:30]>C(O)C.[Pd]>[ClH:30].[N:25]1([C:23]([O:22][CH2:21][CH:9]2[CH2:10][NH:11][CH2:12][CH2:13][NH:8]2)=[O:24])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11794900HCID 11794900, compound

Product 1

HCID 186238032-(1'-Pyrrolidinocarbonyloxymethyl)piperazine hydrochlorideYield 98.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.48 g (3.7 mmol) of 1,4-dibenzyl-2-(1′-pyrrolidinocarbonyloxymethyl)piperazine are dissolved in 40 ml of absolute ethanol and 1 ml of 12N HCl in a 100 ml ground-necked round-bottomed flask. About 100 mg of palladium (10%) on charcoal are added thereto. The mixture is then placed under a hydrogen atmosphere, vigorously stirred and gentle heating is applied (40° C.). When the initial product has disappeared (the reaction program is monitored by thin-layer chromatography eluted with an MeOH/CH2Cl2 mixture (5/95 v/v), after neutralization of an aliquot with a few grains of NaHCO3), the solution is filtered on paper and the catalyst is rinsed several times with ethanol and water. The solvents are then evaporated off under vacuum. 1.04 g of 2-(1′-pyrrolidinocarbonyloxymethyl)piperazine hydrochloride are thus obtained and used in the following step without further purification. Yield: 98.3%. Rf=0.4 (80/20/2 v/v/v CHCl3/MeOH/NH4OH).

Workup

  1. temperaturegentle heating
  2. custom(40° C.)
  3. washeluted with an MeOH/CH2Cl2 mixture (5/95 v/v)
  4. filtrationafter neutralization of an aliquot with a few grains of NaHCO3), the solution is filtered on paper
  5. washthe catalyst is rinsed several times with ethanol and water
  6. customThe solvents are then evaporated off under vacuum

Sources & evidence

ORD record
ord-a77d4450dd1c454998e2451af5419e5f
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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