Diethyl Ether → 1,4-Dibenzylpiperazine-2-carbaldehyde

HRID 2050190Notes

Reaction equation

HRID 2050190 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[C:21](OCC)=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCOCC.[H-].C([Al+]CC(C)C)C(C)C.[OH-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][CH:9]1[CH:21]=[O:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 2736402Ethyl 1,4-dibenzylpiperazine-2-carboxylateHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 154809991,4-Dibenzylpiperazine-2-carbaldehydeYield 127.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5.0 g (13.9 mmoles) of ethyl 1,4-dibenzylpiperazin-2-carboxylate [prepared in the manner described in Helv. Chim. Acta, 298, 2646(1963) by E. Jucker and E. Rissi] in 40 l ml of dry ether is dropwise added 30 ml of a solution of 1.46 moles of diisobutylaluminium hydride in toluene at -56° to -66° C. under nitrogen atmosphere in a period of 15 minutes, and the mixture is stirred at the same temperature for 1 hour. 10% Aqueous sodium hydroxide solution (20 ml) is slowly dropwise added thereto, and the mixture is warmed up to room temperature and extracted with ether. The extract is washed with water, dried over magnesium sulfate and evaporated under reduced pressure to yield 5.2 g of crude 1,4-dibenzyl-2-formylpiperazine.

Workup

  1. customat -56° to -66° C.
  2. customof 15 minutes
  3. extractionextracted with ether
  4. washThe extract is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-5cb3a21036c244668c72fbb7aae9e742
Source dataset
uspto-grants-1980_04
Patent number
US04200628

Reaction notes

Loading…