Benzyl Bromide → N-[4-(1-Benzylpiperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide

HRID 1280761ノート

反応式

HRID 1280761 の反応式
Cl.Cl.[NH:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:23])[CH:15]=[CH:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[K+].[K+].[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>CC(C)=O>[CH2:30]([N:3]1[CH2:8][CH2:7][CH:6]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:23])[CH:15]=[CH:16][C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[CH2:5][CH2:4]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 69451641N-[4-(piperidine-4-yl)butyl]-3-(pyridin-3-yl)-acrylamide Dihydrochloride

生成物 1

HCID 54513378N-[4-(1-Benzylpiperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

6.5 g (180 mmol) N-[4-(piperidin-4-yl)-butyl]-3-(pyridin-3-yl)-acrylamide dihydrochloride (substance 22) are suspended in 80 ml acetone added to 9.9 g (72.0 mmol) potassium carbonate. A solution of 3.4 g (19.8 mmol) benzyl bromide in 10 ml acetone is added dropwise to this mixture at RT and stirred overnight. Subsequently, the suspension is filtered and the filtrate is concentrated under vacuum. The residue is taken up in 100 ml CHCl3 and washed with 30 ml water. The organic phase is dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5 to 90/10) and crystallized from 15 ml acetonitrile after drawing off the solvent. Beige colored crystals with a MP of 88-90° C. were recovered; yield: 1.1 g (16%).

後処理

  1. filtrationSubsequently, the suspension is filtered
  2. concentrationthe filtrate is concentrated under vacuum
  3. washwashed with 30 ml water
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customthe solvent is removed under vacuum
  6. customThe residue is chromatographically purified over silica gel with CHCl3/CH3OH (95/5 to 90/10)
  7. customcrystallized from 15 ml acetonitrile
  8. customBeige colored crystals with a MP of 88-90° C. were recovered

出典と根拠

ORDレコード
ord-a1b9fcf2a2fe49ce82d4f32830fda73f
出典データセット
uspto-grants-2002_09
特許番号
US06451816B1

反応ノート

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