Sodium Hydroxide → (1,4-Dibenzylpiperazin-2-yl)methanol

HRID 2242813Notes

Reaction equation

HRID 2242813 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([CH:11]1[CH2:16][N:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:14][CH2:13][N:12]1[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O.[OH-].[Na+]>O>[CH2:24]([N:12]1[CH2:13][CH2:14][N:15]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:16][CH:11]1[CH2:9][OH:8])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10860321Methyl 1,4-dibenzylpiperazine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

To the suspension of lithium aluminum hydride (1.54 g, 40.6 mmol) was added 1,4-dibenzyl-piperazine-2-carboxylic acid methyl ester (3.00 g, 9.25 mmol) portionwise at room temperature. The reaction mixture was stirred at reflux for 3 hours. After cooled to 0° C., 1.5 ml of water, 1.5 ml of 4N NaOH aq., and 4.5 ml of water was added successively. The mixture was stirred for 1 hour, and the white precipitate was filtered off with celite pad. The filtrate was concentrated in vacuo to give (1,4-dibenzyl-piperazin-2-yl)-methanol (2.74 g, quant.) as a yellow oil: HPLC-MS (ESI): Calcd for C19H24N2O[M+H]+297, found: 297.

Workup

  1. temperatureat reflux for 3 hours
  2. stirringThe mixture was stirred for 1 hour
  3. filtrationthe white precipitate was filtered off with celite pad
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-bddb9b9184b848ada5e1ef4f7d0a346c
Source dataset
uspto-grants-2010_03
Patent number
US07674797B2

Reaction notes

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