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

HRID 456591노트

반응식

HRID 456591 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-679e92658fd84e4f93dbe03db5c747f9
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07186730B2

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