1-Isopropylpiperazine → 1-iso-Propyl-4-(pent-4-yn-1-yl)piperazine

Temperature

80 °C

A mixture of 1-(1-methylethyl)piperazine (6 g, 46.8 mmol), 5-chloro-1-pentyne (4.91 mL, 46.8 mmol) and sodium bicarbonate (3.93 g, 46.8 mmol) in N,N-dimethylformamide (75 mL) was heated at 80° C. overnight. The reaction mixture was cooled to room temperature then partitioned between ether (100 mL) and water (100 mL). The organic phase was washed with brine (25 mL) then dried using a hydrophobic frit and evaporated. The crude material was purified on a 50 g SCX cartridge (preconditioned with MeOH) eluted with MeOH and flushed with 2M NH3/MeOH. The appropriate fractions were concentrated and dried under vacuum to obtain the title compound as a light brown oil (3.22 g).

1. temperatureThe reaction mixture was cooled to room temperature
2. customthen partitioned between ether (100 mL) and water (100 mL)
3. washThe organic phase was washed with brine (25 mL)
4. customthen dried
5. customevaporated
6. customThe crude material was purified on a 50 g SCX cartridge (preconditioned with MeOH)
7. washeluted with MeOH
8. customflushed with 2M NH3/MeOH
9. concentrationThe appropriate fractions were concentrated
10. customdried under vacuum

ORD record

ord-bc467dae779d42d7a9f9dcd2e2b5372d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428512B2