HCID 18623810, compound → HCID 18623791, compound

HRID 1860447Notes

Reaction equation

HRID 1860447 reaction equation
[ClH:1].C([N:9]1[CH2:14][CH2:13][N:12](CC2C=CC=CC=2)[CH2:11][CH:10]1[CH2:22][NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])C1C=CC=CC=1>C(O)(=O)C.[Pd]>[ClH:1].[CH:27]([O:26][C:24]([NH:23][CH2:22][CH:10]1[CH2:11][NH:12][CH2:13][CH2:14][NH:9]1)=[O:25])([CH3:29])[CH3:28]

Participants

4

Reactant 1

HCID 18623810HCID 18623810, compound

Product 1

HCID 18623791HCID 18623791, compoundYield 100.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

32.3 g (71 mmol) of 1,4-dibenzyl-2-isopropyloxycarbonylaminomethylpiperazine hydrochloride are dissolved in 100 ml of acetic acid and 200 mg of palladium (10%) on charcoal are added. Using PARR apparatus, the suspension is stirred and heated at 60° C. under hydrogen pressure (2.7 bar) overnight. The catalyst is filtered off and the solvent is evaporated to give a compound which is crystallized from an ethanol/ether mixture (5/95 v/v) to give 17 g of 2-isopropyloxycarbonylaminomethylpiperazine hydrochloride in the form of white crystals. Yield: 87%. Melting point: 237.1° C. Rf=0.6 (80/20/2 v/v/v CHCl3/MeOH/NH4OH).

Workup

  1. filtrationThe catalyst is filtered off
  2. customthe solvent is evaporated
  3. customto give a compound which
  4. customis crystallized from an ethanol/ether mixture (5/95 v/v)

Sources & evidence

ORD record
ord-41312832b26643f68e824c172049e263
Source dataset
uspto-grants-2003_03
Patent number
US06531476B1

Reaction notes

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