Trifluoroacetic acid → 1-(4-Iodophenyl)cyclopropanamine

HRID 735022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 735022
FC(F)(F)C(O)=O.[I:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([NH:18]C(=O)OC(C)(C)C)[CH2:17][CH2:16]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[I:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2([NH2:18])[CH2:16][CH2:17]2)=[CH:13][CH:14]=1

Komponenten

6

Edukt 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59019959tert-Butyl (1-(4-iodophenyl)cyclopropyl)carbamate

Produkt 1

HCID 231302211-(4-Iodophenyl)cyclopropanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3 mL (38.76 mmol) of trifluoroacetic acid are added to a solution of 1 g (2.78 mmol) of tert-butyl [1-(4-iodophenyl)cyclopropyl]carbamate in 40 mL dichloromethane and stirred for 24 h. Then the solvent is eliminated by rotary evaporation and the residue is combined with toluene and then again eliminated by rotary evaporation. This residue is then added to a solution of 0.39 g (2.8 mmol) of potassium carbonate in 20 mL of water and stirred for 30 minutes at RT. The aqueous phase is extracted with dichloromethane, the organic phase is dried with sodium sulfate and the solvent is eliminated by rotary evaporation. Yield: 0.7 g (97% of theory); C9H10IN (M=259.09); calc.: molecular ion peak (M+H)+: 260; found: molecular ion peak (M+H)+: 260.

Aufarbeitung

  1. customThen the solvent is eliminated by rotary evaporation
  2. customagain eliminated by rotary evaporation
  3. stirringstirred for 30 minutes at RT
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. dry with materialthe organic phase is dried with sodium sulfate
  6. customthe solvent is eliminated by rotary evaporation

Quellen und Nachweise

ORD-Eintrag
ord-9d062bb41e1d459d9318f3d395f08a7a
Quelldatensatz
uspto-grants-2009_09
Patentnummer
US07592373B2

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