2-Chloromethylbenzimidazole → (E)-2-(4-[2-Phenylethenyl]-1,2,3,6-tetrahydropyridin-1-ylmethyl)benzimidazole

HRID 861385

반응식

HRID 861385 반응식
[CH:1]([C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl[CH2:16][C:17]1[NH:18][C:19]2[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=2[N:21]=1.[BH4-].[Na+]>CN(C)C=O.C(O)C>[C:3]1(/[CH:2]=[CH:1]/[C:9]2[CH2:14][CH2:13][N:12]([CH2:16][C:17]3[NH:18][C:19]4[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=4[N:21]=3)[CH2:11][CH:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

참가 물질

6

반응물 3

HCID 785712-ChloromethylbenzimidazoleHCID 1015764-(2-Phenylethenyl)pyridineHCID 4311764Sodium borohydride

생성물 1

HCID 9818342(E)-2-(4-[2-Phenylethenyl]-1,2,3,6-tetrahydropyridin-1-ylmethyl)benzimidazole

시약·촉매·용매 2

HCID 702Ethanol용매HCID 6228Dimethylformamide용매

실험 절차

A solution of 4-styrylpyridine (4.0 g, 22.1 mmol) and 2-chloromethylbenzimidazole (3.7 g, 22.1 mmol) in dimethylformamide (20 ml) was heated at 110°-120° C. under a nitrogen atmosphere for 1.5 hours. The mixture was cooled to room temperature, diluted with ethanol (380 ml) and carefully treated with sodium borohydride (880 mg, 23.2 mmol). The mixture was stirred at room temperature for 2 hours, then heated at reflux for 1 hour before stirring at room temperature overnight. The ethanol was evaporated in vacuo and the residue partitioned between ethyl acetate (100 ml) and sodium carbonate (half saturated, 100 ml). The phases were separated and the aqueous was extracted with ethyl acetate (2×100 ml). The combined organics were washed with water (50 ml) and brine (50 ml), dried (MgSO4) and evaporated in vacuo to give a reddish gummy residue which was purified by flash chromatography (eluting with 5% methanol in dichloromethane) to give a yellow gummy solid. The gum was triturated with ethyl acetate and recrystallised from ethyl acetate to give the title compound as a mustard solid (912 mg, 13%). M.p. 225°-227° C. (EtOAc); (Found: C, 79.74; H, 6.89; N, 13.47. C21H21N3 requires C, 79.97; H, 6.71; N, 13.32%); δH (DMSO-d6) 2.37 (2H, br s, tetrahydropyridinyl CH2), 2.69 (2H, t, J 5.6 Hz, tetrahydropyridinyl CH2), 3.17 (2H, br s, tetrahydropyridinyl CH2), 3.83 (2H, s, NCH2Ar), 5.91 (1H, s, CH=CR), 6.48 (1H, d, J 16.2 Hz, CHCHPh), 6.91 (1H, d, J-16.2 Hz, CHPh), 7.13-7.22 (3H, m, ArH), 7.29-7.33 (2H, m, ArH), 7.42-7.47 (3H, m, ArH), 7.54 (1H, m, ArH), and 12.31 (1H, br s, NH); m/z (CI+, NHs) 316 (M+1)+.

후처리

  1. temperatureheated
  2. temperatureat reflux for 1 hour
  3. stirringbefore stirring at room temperature overnight
  4. customThe ethanol was evaporated in vacuo
  5. customthe residue partitioned between ethyl acetate (100 ml) and sodium carbonate (half saturated, 100 ml)
  6. customThe phases were separated
  7. extractionthe aqueous was extracted with ethyl acetate (2×100 ml)
  8. washThe combined organics were washed with water (50 ml) and brine (50 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo
  11. customto give a reddish gummy residue which
  12. customwas purified by flash chromatography (eluting with 5% methanol in dichloromethane)
  13. customto give a yellow gummy solid
  14. customThe gum was triturated with ethyl acetate
  15. customrecrystallised from ethyl acetate

출처 및 근거

ORD 기록
ord-7c6207828c9a41a8a7fa4cb212f4a5fd
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05714498

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