Triethylamine → 1-Boc-4-(4-ethynylphenyl)piperazine

Temperature

100 °C

A microwave vial was charged with tert-butyl 4-(4-iodophenyl)piperazine-1-carboxylate (300 mg, 0.773 mmol), trimethylsilylacetylene (0.22 mL, 1.54 mmol), NEt3 (3.0 mL), DMF (1.5 mL), CuI (15 mg, 0.080 mmol), and PdCl2(PPh3)2 (27 mg, 0.039 mmol). The vial was capped and heated in the microwave at 100° C. for 1 h. After removing the NEt3 in vacuo, the residue was extracted with EtOAc (15 mL). The organic layer was then washed with NaHCO3 (sat.) (5 mL), H2O (5 mL), brine (5 mL) and then dried over MgSO4. The solvent was removed and then the material was dissolved into MeOH (4 mL) and THF (2 mL). K2CO3 (1.0 mL of a 1M solution) was added and the reaction stirred for 3 h. The solvent was removed and the residue extracted with EtOAc (15 mL). The organic layer was washed with brine (5 mL) and then dried over MgSO4. The solvent was removed and the product dried under high vacuum to give the title compound as a brown solid (212 mg, 96%); MS ESI 287.0 [M+H]+, calcd for [C17H22N2O2+H]+ 287.18.

1. customThe vial was capped
2. customAfter removing the NEt3 in vacuo
3. extractionthe residue was extracted with EtOAc (15 mL)
4. washThe organic layer was then washed with NaHCO3 (sat.) (5 mL), H2O (5 mL), brine (5 mL)
5. dry with materialdried over MgSO4
6. customThe solvent was removed
7. dissolutionthe material was dissolved into MeOH (4 mL) and THF (2 mL)
8. additionK2CO3 (1.0 mL of a 1M solution) was added
9. customThe solvent was removed
10. extractionthe residue extracted with EtOAc (15 mL)
11. washThe organic layer was washed with brine (5 mL)
12. dry with materialdried over MgSO4
13. customThe solvent was removed
14. customthe product dried under high vacuum

ORD record

ord-2f0ec94236d043bbab724cc35f5fb141

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139563B2