Diethyl Ether → (1,4-Dibenzylpiperazin-2-yl)methanol

HRID 1089210Notes

Reaction equation

HRID 1089210 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C(CC[CH:12]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)(O)=O.C[CH2:33][O:34]CC>>[OH:34][CH2:33][CH:12]1[CH2:17][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:15][CH2:14][N:13]1[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 21226445Aluminium lithium hydrideHCID 855762681,4-Bis(phenylmethyl)-2-piperazinepropanoic acid

Product 1

HCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanolYield 86%

Conditions

Temperature
-5 °C

Procedure

In a dry flask were carefully placed 5.67 g (150 mmol) of lithium aluminum hydride to which were added 110 ml of absolute ether. The suspension was flushed with nitrogen and cooled to -5° C. Then a solution of 25 g (73.0 mmol) of 2-carboxyethyl-1,4-di-phenylmethyl piperazine in 110 ml of absolute ether was added dropwise. After complete addition the suspension was heated under reflux for three hours, cooled in an ice-bath. Excess of hydride was carefully destroyed with 6.3 ml of water. Insoluble material was filtered off and the ether layer was washed with water and dried over magnesium sulfate. After removing of the solvent it was obtained 18.85 g. (86%) of title compound. MP 77° C.

Workup

  1. customIn a dry flask were carefully placed
  2. customThe suspension was flushed with nitrogen
  3. additionAfter complete addition the suspension
  4. temperaturewas heated
  5. temperatureunder reflux for three hours
  6. temperaturecooled in an ice-bath
  7. customExcess of hydride was carefully destroyed with 6.3 ml of water
  8. filtrationInsoluble material was filtered off
  9. washthe ether layer was washed with water
  10. dry with materialdried over magnesium sulfate
  11. customAfter removing of the solvent it
  12. customwas obtained 18.85 g

Sources & evidence

ORD record
ord-8baef57e14a9467898ac57bce6a23b01
Source dataset
uspto-grants-1990_10
Patent number
US04965273

Reaction notes

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