Dimethyl Sulfoxide → 1-(3-Phenylpropionyl)-4-ketopiperidine

HRID 1797037ノート

反応式

HRID 1797037 の反応式
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][CH:24]([OH:27])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[C:11]1([CH2:17][CH2:18][C:19]([N:21]2[CH2:26][CH2:25][C:24](=[O:27])[CH2:23][CH2:22]2)=[O:20])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 221751621-(4-Hydroxypiperidin-1-yl)-3-phenylpropan-1-one

生成物 1

HCID 178176121-(3-Phenylpropionyl)-4-ketopiperidine収率 89.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒4 回

実験手順

To 1.68 mL of oxalyl chloride (19.2 mmol) in 35 mL of CH2Cl2 at −78° C. was added 2.73 mL (38.5 mmol) of dry DMSO in 5 mL of CH2Cl2. After the addition, 3.6 g (15.4 mmol) of 1-(3-phenylpropionyl)-4-hydroxypiperidine 134 in 5 mL of CH2Cl2 was added, and the mixture was stirred for 5 min in the cold. 10.73 mL (77 mmol) of triethylamine in 5 mL of CH2Cl2 was added, and the mixture was allowed to come to room temperature. The mixture was quenched with saturated aqueous ammonium chloride solution. The organic phase was washed with water twice, with saturated brine, dried, and evaporated under vacuum to give 3.2 g (89%) of 1-(3-phenylpropionyl)-4-ketopiperidine (135). GC/MS showed 100% purity with a molecular ion of 231.

後処理

  1. additionwas added
  2. customto come to room temperature
  3. customThe mixture was quenched with saturated aqueous ammonium chloride solution
  4. washThe organic phase was washed with water twice
  5. dry with materialwith saturated brine, dried
  6. customevaporated under vacuum

出典と根拠

ORDレコード
ord-e5f2805f6a9d49d1b68d50577321b770
出典データセット
uspto-grants-2006_04
特許番号
US07034035B2

反応ノート

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