Reaction #1833274

Reaction equation

(trans)-2-(4-((2-methoxyethoxy)methoxy)phenyl)cyclopropanamine

Intermediate L

(trans)-2-(4-((2-methoxyethoxy)methoxy)phenyl)cyclopropanamine

p-TsOH.H2O

water

NaOH

→

p-TsOH

4-((trans)-2-aminocyclopropyl)phenol

Solvents

EtOH

Conditions

Workup

1. 1
   Extractionextracted with EtOAc (4×10 mL)
2. 2
   WashThe organic layer was washed with brine (10 mL)
3. 3
   Dryingdried over anhydrous Na2SO4
4. 4
   Filtrationfiltered
5. 5
   OtherAfter removal of the solvent a brownish residue

Procedure

A solution of (trans)-2-(4-((2-methoxyethoxy)methoxy)phenyl)cyclopropanamine (Intermediate L, 62 mg, 0.26 mmol) and p-TsOH.H2O (60 mg, 0.31 mmol) in EtOH (5 mL) was heated at 75° C. for 2 h. The pH of the reaction was adjusted to 7 with NaOH (10% aqueous solution), the mixture was poured into water (10 mL) and extracted with EtOAc (4×10 mL). The organic layer was washed with brine (10 mL), dried over anhydrous Na2SO4 and filtered. After removal of the solvent a brownish residue was obtained (44 mg, 4-((trans)-2-aminocyclopropyl)phenol contaminated with p-TsOH) that was used in the next step without further purification.

Source