Trifluoroacetic acid → 4-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

HRID 1491683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1491683
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1)=[O:11].C(C(O)=O)(F)(F)F.I[CH2:26][CH2:27][CH2:28][O:29][C:30]1[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=1.C(=O)([O-])O.[Na+]>C(OCC)(=O)C.O.O1CCCC1>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([CH:12]1[CH2:17][CH2:16][N:15]([CH2:26][CH2:27][CH2:28][O:29][C:30]2[CH:39]=[CH:38][C:33]([C:34]([O:36][CH3:37])=[O:35])=[CH:32][CH:31]=2)[CH2:14][CH2:13]1)=[O:11]

Komponenten

8

Edukt 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 152370094-(Benzthiazole-2-carbonyl)piperidineHCID 153374624-(3-Iodopropoxy)benzoic acid, methyl ester

Produkt 1

HCID 153374634-[3-[4-[(2-Benzothiazolyl)carbonyl]-1-piperidinyl]propoxy]benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Mix (2-benzothiazolyl)(4-piperidinyl)methanone.CF3CO2H (7.08 g, 19.7mmol), 4-(3-iodopropoxy)benzoic acid, methyl ester (6.50 g, 20.3 mmol), sodium hydrogen carbonate (3.41 g, 40.6 mmol), tetrahydrofuran (100 mL) and water (20 mL). Heat at reflux under an argon atmosphere overnight. Cool to room temperature, dilute with ethyl acetate (150 mL), wash with 10% sodium hydrogen carbonate (50 mL), water (2×50 mL) and saturated sodium chloride (50 mL). Dry (MgSO4), evaporate the solvent in vacuo and triturate with hexane. Collect the solid by filtration and recrystallize (methanol) to give the title compound as a pale yellow solid; mp 108°-109.5° C.

Aufarbeitung

  1. temperatureHeat
  2. temperatureat reflux under an argon atmosphere overnight
  3. washwash with 10% sodium hydrogen carbonate (50 mL), water (2×50 mL) and saturated sodium chloride (50 mL)
  4. dry with materialDry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customtriturate with hexane
  7. customCollect the solid
  8. filtrationby filtration
  9. customrecrystallize (methanol)

Quellen und Nachweise

ORD-Eintrag
ord-c9468f2281ee4a5b83b5b93f9ef0f8ae
Quelldatensatz
uspto-grants-1994_12
Patentnummer
US05371093

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