Ethyl 1,4-dibenzylpiperazine-2-carboxylate → (1,4-Dibenzylpiperazin-2-yl)methanol

HRID 968648Notes

Reaction equation

HRID 968648 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([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)C>O1CCCC1>[CH2:25]([N:13]1[CH2:14][CH2:15][N:16]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:17][CH:12]1[CH2:10][OH:9])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10827800(1,4-Dibenzylpiperazin-2-yl)methanolYield 87.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (1 M solution in tetrahydrofuran, 32 ml, 32 mmol) at 0° C. was treated dropwise with a solution of 1,4-dibenzyl-piperazine-2-carboxylic acid ethyl ester (10 g, 32.1 mmol) in tetrahydrofuran (30 ml) and stirred for 16 hours. The mixture was quenched by slow addition of sodium hydroxide solution (4 M, 150 ml), followed by dichloromethane (200 ml). The organic phase was separated, dried with sodium sulfate and evaporated to afford 1,4-dibenzyl-2-(hydroxymethyl)piperazine (8.36 g) as an orange oil.

Workup

  1. customThe mixture was quenched by slow addition of sodium hydroxide solution (4 M, 150 ml)
  2. customThe organic phase was separated
  3. dry with materialdried with sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-c2a3eb0f67154f1188ea22c13bbda9e7
Source dataset
uspto-grants-2007_12
Patent number
US07304064B2

Reaction notes

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