HCID 10337444, compound → HCID 10015093, compound

HRID 2396450Notes

Reaction equation

HRID 2396450 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([O:23][CH3:24])[C:16]=2[OH:25])[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[Pd]>[OH:25][C:16]1[C:17]([O:23][CH3:24])=[C:18]([O:21][CH3:22])[CH:19]=[CH:20][C:15]=1[CH2:14][N:11]1[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

4

Reactant 1

HCID 10337444HCID 10337444, compound

Product 1

HCID 10015093HCID 10015093, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

##STR7## 6.8 g (0.02 mol) of N-benzyl-N'-(2-hydroxy-3,4-dimethoxy-benzyl)-piperazine are dissolved in 200 ml of ethanol at 60° C. 1.1 g of 5% palladium on carbon are added thereto and the whole is hydrogenated under a pressure of 5,500 hPa, after which the alcoholic solution is filtered and the solvent is distilled off. The oil obtained is chromatographed on 150 g of silica. A first elution with dichloromethane removes the lower polarity impurities from the mixture. The silica is then washed with a CH2C2 /CH3OH mixture (90/10). 3.78 g of N-(2-hydroxy-3,4-dimethoxybenzyl)-piperazine are obtained (60% yield), and the compound is then converted into its dihydrochloride (m.p. >190° C.) by adding twice the stoichiometric amount of HCl.

Workup

  1. filtrationafter which the alcoholic solution is filtered
  2. distillationthe solvent is distilled off
  3. customThe oil obtained
  4. customis chromatographed on 150 g of silica
  5. washA first elution with dichloromethane
  6. customremoves the lower polarity impurities from the mixture
  7. washThe silica is then washed with a CH2C2 /CH3OH mixture (90/10)

Sources & evidence

ORD record
ord-051ddf85a2f047a495281a6e6537415e
Source dataset
uspto-grants-1996_02
Patent number
US05492913

Reaction notes

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