2-Allyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol → 2-n-Propyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol

HRID 864857ノート

反応式

HRID 864857 の反応式
[CH2:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:22])[CH:2]=[CH2:3].[H][H]>C(O)C.Cl.[Pd]>[CH2:1]([C:4]1[CH:9]=[C:8]([N:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[CH2:12][CH2:11]2)[CH:7]=[CH:6][C:5]=1[OH:22])[CH2:2][CH3:3]

参加物

6

反応物 2

HCID 189184412-Allyl-4-[4-(4-pyridyl)piperazin-1-yl]phenolHCID 178418361HCID 178418361、化合物

生成物 1

HCID 189186162-n-Propyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol収率 94%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 313Hydrochloric Acid溶媒HCID 702Ethanol溶媒

実験手順

The product from Example 205, step (ii) (0.74 g) in ethanol (25 ml) and 1N hydrochloric acid (2.5 ml) was hydrogenated at room temperature and atmospheric pressure over 10% palladium charcoal (0.15 g) until uptake of hydrogen was complete. Catalyst was removed by filtration through diatomaceous earth and the filtrate evaporated. The residue was triturated with a mixture of ethyl acetate (25 ml) and saturated sodium bicarbonate solution (25 ml) and the insoluble solid was filtered and washed with water and ethyl acetate. The aqueous layer of the filtrate was extracted twice with dichloromethane and the combined organic extracts evaporated. The residue was combined with the ethyl acetate-insoluble material and treated with boiling ethanol (40 ml), unsoluble material being removed by filtration. Evaportion of the filtrate gave 2-n-propyl-4-[4-(4-pyridyl)piperazin-1-yl]phenol (0.7 g) as a solid NMR (d6DMSO) δ8.84-8.68(1H,m), 8.18(2H,d), 6.82(2H,m), 6.7(3H,m), 4.1(1H,m), 3.42(4H,t), 3.17(3H,s), 3.05(4H,t), 2.48(DMSO), 1.55(2H,m), 0.89(3H,t).

後処理

  1. customwas hydrogenated at room temperature
  2. customCatalyst was removed by filtration through diatomaceous earth
  3. customthe filtrate evaporated
  4. customThe residue was triturated with a mixture of ethyl acetate (25 ml) and saturated sodium bicarbonate solution (25 ml)
  5. filtrationthe insoluble solid was filtered
  6. washwashed with water and ethyl acetate
  7. extractionThe aqueous layer of the filtrate was extracted twice with dichloromethane
  8. customthe combined organic extracts evaporated
  9. additiontreated with boiling ethanol (40 ml), unsoluble material
  10. custombeing removed by filtration

出典と根拠

ORDレコード
ord-8345dda7a87c4528a2fa08b38f339a3f
出典データセット
uspto-grants-1996_10
特許番号
US05563141

反応ノート

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