Trifluoroacetic acid → 1-(4-Iodophenyl)cyclopropanamine

HRID 735022Notes

Reaction equation

HRID 735022 reaction equation
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

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59019959HCID 59019959, compound

Product 1

HCID 231302211-(4-Iodophenyl)cyclopropanamine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9d062bb41e1d459d9318f3d395f08a7a
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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