Water → 2-Phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 250737

반응식

HRID 250737 반응식
Cl.[NH:2]=[C:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O.C(=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[C:12]1([C:10]2[N:2]=[C:3]3[CH2:7][CH2:6][CH2:5][N:4]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 10340Sodium CarbonateHCID 178479085HCID 178479085, 화합물

생성물 1

HCID 7655112-Phenyl-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole수율 90%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Combine 2-iminopyrrolidine hydrochloride (6.98 g, 57.8 mmol) (Callahan, et al., J. Med. Chem. 45, 999-1001 (2002)), 2-bromoacetophenone (3.8 g, 19.3 mmol), and sodium carbonate (8.2 g, 77.2 mmol) in dry dimethylformamide (25 mL). Heat at 80° C. for 18 hours. Cool to room temperature, add water (60 mL), and extract with ethyl acetate (3×100 mL). Concentrate the combined organic layers under reduced pressure. Dilute the residue with diethyl ether (100 mL), wash with cold water (3×80 mL), and concentrate under reduced pressure to provide the desired compound as a white solid (3.2 g, 89%).

후처리

  1. temperatureCool to room temperature
  2. extractionextract with ethyl acetate (3×100 mL)
  3. concentrationConcentrate the combined organic layers under reduced pressure
  4. additionDilute the residue with diethyl ether (100 mL)
  5. washwash with cold water (3×80 mL)
  6. concentrationconcentrate under reduced pressure

출처 및 근거

ORD 기록
ord-86e038ca51c64e73b5384b65ff45a87a
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863310B2

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