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

HRID 22261

反応式

HRID 22261 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-b1edf5cbf45746debeb10b6d854d0415
出典データセット
uspto-grants-1995_06
特許番号
US05428037

関連ノート

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