Potassium Carbonate → (1,4-Dibenzylpiperazin-2-yl)methanol

HRID 2165598Notes

Reaction equation

HRID 2165598 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]1([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH:15]2[C:27](OCC)=[O:28])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[OH-].[K+].C(=O)([O-])[O-].[K+].[K+]>CCOCC>[C:7]1([CH2:13][N:14]2[CH2:19][CH2:18][N:17]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH2:16][CH:15]2[CH2:27][OH:28])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanolYield 103.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A 3.06 g portion of lithium aluminum hydride in 130 ml of dry ether, with argon bubbling through the solution, was stirred at room temperature. A solution of 24.5 g of 1,4-bis(phenylmethyl)-2-piperazinecarboxylic acid, ethyl ester in 125 ml of dry ether was added, the mixture was heated at reflux for 5 hours and then cooled. A 40 ml portion of 40% aqueous potassium hydroxide followed by 80 ml of saturated aqueous potassium carbonate were added dropwise, under argon. The mixture was allowed to stand overnight, after stirring for one hour. The ether layer was removed and saved, then the remainder filtered. The filtrate was extracted several times with ether. The ether solutions were combined, dried, filtered and evaporated, giving 22.15 g of 1,4-bis(phenylmethyl)2-piperazinemethanol as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 5 hours
  3. temperaturecooled
  4. additionwere added dropwise, under argon
  5. customThe ether layer was removed
  6. filtrationthe remainder filtered
  7. extractionThe filtrate was extracted several times with ether
  8. customdried
  9. filtrationfiltered
  10. customevaporated

Sources & evidence

ORD record
ord-85b4b9ed47a44ab8b459d1fd611a6885
Source dataset
uspto-grants-1990_07
Patent number
US04940710

Reaction notes

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