Dimethylformamide → 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzaldehyde

HRID 1091378Notes

Reaction equation

HRID 1091378 reaction equation
C([Li])CCC.[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][C@@H:14]1[C:26]1[CH:31]=[CH:30][C:29](Br)=[CH:28][CH:27]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CN(C)[CH:35]=[O:36]>O1CCCC1>[CH2:6]([N:13]1[CH2:18][CH2:17][N:16]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:15][C@@H:14]1[C:26]1[CH:31]=[CH:30][C:29]([CH:35]=[O:36])=[CH:28][CH:27]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 66594629(2S)-1,4-dibenzyl-2-(4-bromophenyl)piperazineHCID 178418339Butyllithium

Product 1

HCID 866345574-((2S)-1,4-dibenzylpiperazin-2-yl)benzaldehydeYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

n-Butyllithium (1.56M in hexane, 14 ml, 21.8 mmol) was added to a solution of (2S)-1,4-dibenzyl-2-(4-bromophenyl)piperazine (6.1 g, 14.5 mmol) in tetrahydrofuran (60 ml) at −78° C. After one hour stirring, dimethylformamide (1.6 g, 21.9 mmol) was added and the solution was stirred for one hour. The mixture was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting 5-10% methanol in chloroform to furnish 4-((2S)-1,4-dibenzylpiperazin-2-yl)benzaldehyde (1.6 g, 41%) as a colorless oil.

Workup

  1. stirringthe solution was stirred for one hour
  2. customThe mixture was partitioned between water and chloroform
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting 5-10% methanol in chloroform

Sources & evidence

ORD record
ord-e15847031e8e45eaa77ca1fcf6e68f9d
Source dataset
uspto-grants-2012_03
Patent number
US08129377B2

Reaction notes

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