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

HRID 1091378노트

반응식

HRID 1091378 반응식
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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e15847031e8e45eaa77ca1fcf6e68f9d
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129377B2

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