Ethylenediamine → 2-(4-methoxyphenyl)piperazine

HRID 1784656Notes

Reaction equation

HRID 1784656 reaction equation
[CH2:1]([NH2:4])[CH2:2][NH2:3].[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([CH:15]=O)=O)=[CH:9][CH:8]=1.[BH4-].[Na+]>CO.O1CCCC1>[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:15][NH:4][CH2:1][CH2:2][NH:3]2)=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 3301EthylenediamineHCID 70643(4-Methoxyphenyl)glyoxalHCID 4311764Sodium borohydride

Product 1

HCID 27717532-(4-methoxyphenyl)piperazineYield 45.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent3×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methanol (5 ml) solution of ethylenediamine (3.74 g, 62.29 mmol) was added to the ice-cooled solution of 4-methoxyphenylglyoxal (8.30 g, 45.5 mmol) in methanol (100 ml) and tetrahydrofuran (50 ml) and stirred for 10 min. After cooling to 0° C., sodium tetrahydroborate (6.14 g, 162.2 mmol) and additional methanol (50 ml) was added and stirred overnight. After removal of the solvent, aqueous sodium hydroxide was added and was extracted with dichloromethane three times and washed with brine and dried over sodium sulfate. After removal of the solvent, purification of the residue by silica gel column chromatography (eluent; dichloromethane/ethanol/diethylamine=20/2/1) gave 2-(4-methoxypheny)-piperazine (3.96 g, 45%).

Workup

  1. stirringstirred overnight
  2. customAfter removal of the solvent, aqueous sodium hydroxide
  3. additionwas added
  4. extractionwas extracted with dichloromethane three times
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customAfter removal of the solvent, purification of the residue by silica gel column chromatography (eluent; dichloromethane/ethanol/diethylamine=20/2/1)

Sources & evidence

ORD record
ord-1bb930f324334d69b46eb823f018c576
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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