Hydrochloric Acid → 2-Chloro-4-(4-phenethylpiperazin-1-yl)phenol

HRID 269880Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269880
[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[CH2:14][CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8]COC.CC(O)C.Cl.C(=O)([O-])O.[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:12]2[CH2:13][CH2:14][N:15]([CH2:18][CH2:19][C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:16][CH2:17]2)[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 516892Sodium BicarbonateHCID 231114421-(3-Chloro-4-methoxymethoxyphenyl)-4-phenethylpiperazine

Produkt 1

HCID 231114392-Chloro-4-(4-phenethylpiperazin-1-yl)phenolAusbeute 49,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 1-(3-chloro-4-methoxymethoxyphenyl)-4-phenethyl-piperazine (214 mg), 2-propanol (1 mL) and tetrahydrofuran (1 mL) were added, followed by cooling with ice and addition of conc. hydrochloric acid (0.5 mL). Raising the temperature back to the ambient level, the mixture was stirred for 4.5 hours. The reaction mixture was poured in saturated saline solution, rendered weakly alkaline with saturated aqueous sodium hydrogencarbonate solution, and the product was extracted with ethyl acetate. The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the resulting crude product was purified on TLC (developer, chloroform: acetone=5:1) to provide 2-chloro-4-(4-phenethylpiperazin-1-yl)phenol (93 mg).

Aufarbeitung

  1. temperatureRaising the temperature back to the ambient level
  2. additionThe reaction mixture was poured in saturated saline solution
  3. extractionthe product was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off
  7. customthe resulting crude product was purified on TLC (developer, chloroform: acetone=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-c1e10cd075a84d2a9e50adc5cb1d037a
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07449466B2

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