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

HRID 1091378ノート

反応式

HRID 1091378 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e15847031e8e45eaa77ca1fcf6e68f9d
出典データセット
uspto-grants-2012_03
特許番号
US08129377B2

反応ノート

読み込み中…