Hydrochloric Acid → 1-[2-(4-Fluoro-1H-benzoimidazol-2-yl)-ethyl]-piperidine-4-carboxylic acid ethyl ester

HRID 456591ノート

反応式

HRID 456591 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][C:14]#[N:15])[CH2:8][CH2:7]1)=[O:5])[CH3:2].C(O)C.Cl.[F:20][C:21]1[C:22](N)=[C:23]([NH2:27])[CH:24]=[CH:25][CH:26]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([CH2:12][CH2:13][C:14]2[NH:27][C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([F:20])[C:22]=3[N:15]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 27828353-Fluorobenzene-1,2-diamineHCID 43084552Ethyl 1-(2-cyanoethyl)piperidine-4-carboxylate

生成物 1

HCID 695222001-[2-(4-Fluoro-1H-benzoimidazol-2-yl)-ethyl]-piperidine-4-carboxylic acid ethyl ester収率 55%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

A solution of (a) (6.4 g, 30 mmol) and ethanol (2.1 ml, 40 mmol) in chloroform (60 ml) was saturated with gaseous hydrochloric acid at 0° C. for 0.5 hours. The mixture was left 20 hours at 4° C. then concentrated in vacuo to afford a white foam. This was suspended in chloroform (60 ml), treated with 3-fluorophenylenediamine (3.8 g, 30 mmol) and heated under reflux for 1 hour. The mixture was poured onto water. The aqueous phase was then basified with sodium bicarbonate and extracted three times with dichloromethane. The organic extract was washed with water, brine, dried over magnesium sulfate and evaporated. The resulting residue was triturated with ethyl acetate, then diethyl ether to give a white solid (5.2 g, 55%).

後処理

  1. concentrationthen concentrated in vacuo
  2. customto afford a white foam
  3. temperatureheated
  4. temperatureunder reflux for 1 hour
  5. additionThe mixture was poured onto water
  6. extractionextracted three times with dichloromethane
  7. extractionThe organic extract
  8. washwas washed with water, brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated
  11. customThe resulting residue was triturated with ethyl acetate

出典と根拠

ORDレコード
ord-679e92658fd84e4f93dbe03db5c747f9
出典データセット
uspto-grants-2007_03
特許番号
US07186730B2

反応ノート

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