Benzathine → Methyl 2-(1,4-dibenzylpiperazin-2-yl)acetate

HRID 352763

反応式

HRID 352763 の反応式
Br/[C:2](/[CH3:8])=[CH:3]\[C:4]([O:6][CH3:7])=[O:5].[CH2:9]([NH:16][CH2:17][CH2:18][NH:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1(C)C=CC=CC=1.C(N(CC)CC)C>[CH2:9]([N:16]1[CH2:17][CH2:18][N:19]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:8][CH:2]1[CH2:3][C:4]([O:6][CH3:7])=[O:5])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

参加物

5

反応物 2

HCID 8793BenzathineHCID 12625788Methyl 3-bromocrotonate

生成物 1

HCID 22710010Methyl 2-(1,4-dibenzylpiperazin-2-yl)acetate

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8471Triethylamine溶媒2 回

実験手順

In toluene (250 ml), N,N′-dibenzylethylenediamine (12 ml) and triethylamine (12 ml) were dissolved, followed by the dropwise addition of methyl 3-bromocrotonate (7.0 ml) under ice cooling. The resulting mixture was stirred at room temperature for 24 hours. After the addition of triethylamine (2.0 ml), the resulting mixture was stirred at room temperature for 71 hours. The insoluble matter was filtered off and the filtrate was distilled under reduced pressure. The residue was added with 10% hydrochloric acid (300 ml) and crystals so precipitated were removed by filtration. Ethyl acetate was added to the filtrate. Potassium carbonate was added to the water layer so separated to make it alkaline. Ethyl acetate was added to the resulting mixture. The organic layer so separated was washed with saturated aqueous NaCl solution and dried over anhydrous potassium carbonate. The solvent was then distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column (hexane ethyl acetate=4:1), whereby the title compound (10.7 g, 62%) was obtained.

後処理

  1. stirringthe resulting mixture was stirred at room temperature for 71 hours
  2. filtrationThe insoluble matter was filtered off
  3. distillationthe filtrate was distilled under reduced pressure
  4. additionThe residue was added with 10% hydrochloric acid (300 ml) and crystals
  5. customso precipitated
  6. customwere removed by filtration
  7. additionEthyl acetate was added to the filtrate
  8. additionPotassium carbonate was added to the water layer
  9. customso separated
  10. additionEthyl acetate was added to the resulting mixture
  11. customThe organic layer so separated
  12. washwas washed with saturated aqueous NaCl solution
  13. dry with materialdried over anhydrous potassium carbonate
  14. distillationThe solvent was then distilled off under reduced pressure
  15. customThe residue was purified by chromatography on a silica gel column (hexane ethyl acetate=4:1), whereby the title compound (10.7 g, 62%)
  16. customwas obtained

出典と根拠

ORDレコード
ord-7ff5fd888bf44a5f9c11c240e711a0f0
出典データセット
uspto-grants-2004_06
特許番号
US06747023B1

関連ノート

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