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

HRID 1091378Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1091378
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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e15847031e8e45eaa77ca1fcf6e68f9d
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08129377B2

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