Sodium Carbonate → 2-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

HRID 359715

반응식

HRID 359715 반응식
Br.Br[CH2:3][C:4]([C:6]1[CH:11]=[CH:10][N:9]=[CH:8][CH:7]=1)=O.Cl.[NH:13]=[C:14]1[CH2:18][CH2:17][CH2:16][NH:15]1.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[N:9]1[CH:10]=[CH:11][C:6]([C:4]2[N:13]=[C:14]3[CH2:18][CH2:17][CH2:16][N:15]3[CH:3]=2)=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 178479085HCID 178479085, 화합물

생성물 1

HCID 198792362-(pyridin-4-yl)-6,7-dihydro-5H-pyrrolo[1,2-a]imidazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A stirred suspension of 10q (35.6 mmoles) of 4-(bromoacetyl) pyridine hydrobromide and 12.9 q (107 mmoles) of 2-imino-pyrrolidine hydrochloride in 100 ml of dry dimethylformamide was treated with 18.9 q (178 mmoles) of anhydrous sodium carbonate. This suspension was heated at 80° C. overnight in an oil bath. The solvent was removed in vacuo, the residue dissolved in water and extracted with chloroform. The organic layer was washed three times with water, dried over anhydrous potassium carbonate and stripped in vacuo. The residue was chromatographed on silica and eluted with 10-15% methanol in methylene chloride acetone (85:15). This fraction was stripped in vacuo and the solid residue recrystallized twice from ethyl acetate to afford the desired titled compound, mp 140-141° C., 1HNMR (250 MHz, CDCl3) δ8 62 (2H,d), 7.60(2H,d), 7.34(lH,s), 4.04(2H,t), 2.95 (2H,t), 2.64(2H,q).

후처리

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with chloroform
  4. washThe organic layer was washed three times with water
  5. dry with materialdried over anhydrous potassium carbonate
  6. customThe residue was chromatographed on silica
  7. washeluted with 10-15% methanol in methylene chloride acetone (85:15)
  8. customthe solid residue recrystallized twice from ethyl acetate

출처 및 근거

ORD 기록
ord-f7504d283a4c4f68a3103426b9c95171
출처 데이터셋
uspto-grants-1991_03
특허 번호
US05002941

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