Acetyl chloride → 1-(4-(4-bromo-1H-pyrazol-1-yl)piperidin-1-yl)ethanone

HRID 216723ノート

反応式

HRID 216723 の反応式
[C:1](Cl)(=[O:3])[CH3:2].[Br:5][C:6]1[CH:7]=[N:8][N:9]([CH:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:10]=1.CCN(CC)CC>C(Cl)Cl>[Br:5][C:6]1[CH:7]=[N:8][N:9]([CH:11]2[CH2:16][CH2:15][N:14]([C:1](=[O:3])[CH3:2])[CH2:13][CH2:12]2)[CH:10]=1

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 521916214-(4-Bromo-1H-pyrazol-1-yl)piperidine

生成物 1

HCID 593926411-(4-(4-bromo-1H-pyrazol-1-yl)piperidin-1-yl)ethanone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Acetyl chloride (312 μl, 4.35 mmol) is added dropwise, under stirring at 0° C., to a solution of 4-(4-Bromo-pyrazol-1-yl)-piperidine (as obtained in preparation 89, 1 g, 4.34 mmol), Et3N (1.824 ml, 13.04 mmol) in CH2Cl2. The cooling bath is then removed and the reaction mixture stirred at RT for an additional 1 h. The mixture is then diluted with de-ionized water and the phases are separated. The organic phase is washed several times with de-ionized water and the aqueous layer re-extracted with CH2Cl2. The combined organic layers are washed with brine, dried over Na2SO4, filtered and the filtrate is concentrated in vacuo. The residue is used without further purification in the next step, and afford the title compound as yellow solid, Rt=0.786 min (Acquity HPLC BEH C18, 2.1×50 mm, 1.7 micron, detection 215 nM, 0.1 min 2% CH3CN in H2O, 2% to 100% CH3CN in H2O in 1.5 min, 0.4 min 100% CH3CN+0.1% TFA, flow rate 1.0 ml/min); MS: 272 (M+1, 79Br)+

後処理

  1. customThe cooling bath is then removed
  2. additionThe mixture is then diluted with de-ionized water
  3. customthe phases are separated
  4. washThe organic phase is washed several times with de-ionized water
  5. extractionthe aqueous layer re-extracted with CH2Cl2
  6. washThe combined organic layers are washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is used without further purification in the next step

出典と根拠

ORDレコード
ord-bc29c9538c6e467f91e55eab0b50a306
出典データセット
uspto-grants-2012_06
特許番号
US08193189B2

反応ノート

読み込み中…