Reaction #657340

Reaction equation

[3-(4-{7-[2-(3-fluoro-phenyl)-ethyl]-2-oxo-2,9-dihydro-10-oxa-1,3,9-triaza-anthracen-3-yl}-piperidin-1-yl)-propyl]-carbamic acid tert-butyl ester

trifluoroacetic acid

→

desired product

Yield 99.0%

3-[1-(3-Amino-propyl)-piperidin-4-yl]-7-[2-(3-fluoro-phenyl)-ethyl]-3H,9H-10-oxa-1,3,9-triaza-anthracen-2-one

Yield 99.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   Concentrationthen concentrated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water (10 mL)
3. 3
   workup.ADDITIONthen treated with 1.0 N aqueous hydrochloric acid (2.0 mL)
4. 4
   ConcentrationThe resulting solution was concentrated
5. 5
   workup.DISSOLUTIONthe residue was re-dissolved in water (10 mL)
6. 6
   workup.ADDITIONtreated with hydrochloric acid (2.0 mL)
7. 7
   Concentrationconcentrated
8. 8
   workup.DISSOLUTIONThe residue was dissolved in water (10 mL)
9. 9
   Temperaturethe resulting solution was frozen

Procedure

To a solution of [3-(4-{7-[2-(3-fluoro-phenyl)-ethyl]-2-oxo-2,9-dihydro-10-oxa-1,3,9-triaza-anthracen-3-yl}-piperidin-1-yl)-propyl]-carbamic acid tert-butyl ester (94 mg, 0.167 mmol, 1 equiv) in dichloromethane (10 mL) at 23° C. was added trifluoroacetic acid (4.0 mL). The reaction was stirred for 30 min then concentrated. The residue was dissolved in water (10 mL) then treated with 1.0 N aqueous hydrochloric acid (2.0 mL). The resulting solution was concentrated, and then the residue was re-dissolved in water (10 mL), treated with hydrochloric acid (2.0 mL) and concentrated. The residue was dissolved in water (10 mL) and then the resulting solution was frozen and then lyophilized to give 88 mg (0.165 mmol, 99%) of the desired product (dihydrochloride salt) as a yellow solid. LCMS (EI): 464.1 (M+H)+.

Source