Sodium Hydroxide → 1-(2,3,4-Trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)methyl]piperazine

HRID 22261

반응식

HRID 22261 반응식
[CH3:1][N:2]1[C:6]([CH3:7])=[C:5]([CH:8]=O)[N:4]=[C:3]1[C:10]1[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=1.[CH3:20][O:21][C:22]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[CH:24][C:23]=1[CH2:32][N:33]1[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]1.C([BH3-])#N.[Na+].[OH-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].C(O)C>[CH3:20][O:21][C:22]1[C:27]([O:28][CH3:29])=[C:26]([O:30][CH3:31])[CH:25]=[CH:24][C:23]=1[CH2:32][N:33]1[CH2:34][CH2:35][N:36]([CH2:8][C:5]2[N:4]=[C:3]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:17])([F:18])[F:19])=[CH:12][CH:11]=3)[N:2]([CH3:1])[C:6]=2[CH3:7])[CH2:37][CH2:38]1

참가 물질

7

반응물 4

HCID 14798Sodium HydroxideHCID 21109TrimetazidineHCID 5003444Sodium cyanoborohydrideHCID 152882331,5-Dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazole

생성물 1

HCID 152882341-(2,3,4-Trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)methyl]piperazine수율 46.6%

시약·촉매·용매 2

HCID 11026Titanium isopropoxide촉매HCID 702Ethanol용매

실험 절차

A solution of 1,5-dimethyl-4-formyl-2-(4-trifluoromethylphenyl)imidazole (0.5 g), 1-(2,3,4-trimethoxyphenylmethyl)piperazine (0.54 g), and titanium(IV)isopropoxide (0.73 g) was allowed to stand for 1 hour at room temperature. Ethanol (10 ml) was added, and the resultant solution was stirred for 1 hour. Sodium cyanoborohydride (90 mg) was then added, and the mixture stirred overnight. Sodium hydroxide was then added until the pH was just over 7, the solvent removed under reduced pressure, and the residue partitioned between methylene chloride/water. The mixture was filtered, the organic layer separated, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel, eluting with ethyl acetate/methanol/ammonia (97/3/0.5), to yield 0.45 g of 1-(2,3,4-trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)methyl]piperazine. Treatment with anhydrous hydrochloric acid in ethanol converted the base to its dihydrochloride salt, m.p. 235° C.

후처리

  1. customthe solvent removed under reduced pressure
  2. customthe residue partitioned between methylene chloride/water
  3. filtrationThe mixture was filtered
  4. customthe organic layer separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was flash-chromatographed on silica gel
  9. washeluting with ethyl acetate/methanol/ammonia (97/3/0.5)

출처 및 근거

ORD 기록
ord-b1edf5cbf45746debeb10b6d854d0415
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428037

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