Water → 1-[3,3-Bis-(2-pyridyl)propyl]-4-(2-methoxyphenyl)piperazine

HRID 2181636Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2181636
C([C:3]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1)#N.S(=O)(=O)(O)O.O.[OH-].[Na+]>C(OCC)(=O)C>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[CH:3]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1)[CH2:4][CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[CH2:8][CH2:7]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 224821111-[3-Cyano-3,3-bis-(2-pyridyl)propyl]-4-(2-methoxyphenyl)piperazine

Produkt 1

HCID 99083481-[3,3-Bis-(2-pyridyl)propyl]-4-(2-methoxyphenyl)piperazineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
125 °C

Versuchsvorschrift

A mixture of 2.44 g of compound of Example 6 and 12 mL of 70% sulphuric acid was stirred for 1.5 h at 125° C. The obtained reaction mixture was then cooled to room temperature, followed by careful pouring into 100 g of ice, dilution with water, alkalinization with 35% sodium hydroxide, and extraction with ethyl acetate (3×40 mL). The combined organic phases were then washed with water, dried on anhydrous sodium sulphate, and then evaporated to complete dryness under vacuum. The obtained crude was then purified by flash chromatography (ethyl acetate-2.2 N solution of ammonia in methanol 9.6:0.4). The recovered fractions were then evaporated to complete dryness, affording 1.87 g of the title product (82%).

Aufarbeitung

  1. customThe obtained reaction mixture
  2. temperaturewas then cooled to room temperature
  3. washThe combined organic phases were then washed with water
  4. dry with materialdried on anhydrous sodium sulphate
  5. customevaporated
  6. customThe obtained crude
  7. customwas then purified by flash chromatography (ethyl acetate-2.2 N solution of ammonia in methanol 9.6:0.4)
  8. customThe recovered fractions were then evaporated

Quellen und Nachweise

ORD-Eintrag
ord-1e3c101444d14e41be438836aa3dfe43
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06894052B1

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