1-Bromo-2-Chloroethane → HCID 21250993, compound

A mixture of 4-(4-fluorobenzamido)piperidine (2 g; preparation 2), triethylamine (3.75 ml) and 1-bromo-2-chloroethane (1.11 ml) in 150 ml of dry tetrahydrofuran was refluxed overnight, then further triethylamine (3.75 ml) and 1-bromo-2-chloroethane (1.11 ml) were added. The mixture was refluxed for an additional 5 hours, treated again with 3.75 ml of triethylamine and 1.11 ml of 1-bromo-2-chloroethane and refluxed overnight. The reaction mixture was concentrated to a small volume, treated with ethyl acetate (200 ml) and the mixture washed with an aqueous saturated potassium carbonate solution. The organic phase was dried over sodium sulfate and concentrated to dryness. The residue (1.3 g) was crystallized from 10 ml of diethyl ether and dried under vacuum at 50° C., to give 1.06 g of the product, m.p. 220-225° C.

1. temperaturewas refluxed overnight
2. temperatureThe mixture was refluxed for an additional 5 hours
3. temperaturerefluxed overnight
4. concentrationThe reaction mixture was concentrated to a small volume
5. additiontreated with ethyl acetate (200 ml)
6. washthe mixture washed with an aqueous saturated potassium carbonate solution
7. dry with materialThe organic phase was dried over sodium sulfate
8. concentrationconcentrated to dryness
9. customThe residue (1.3 g) was crystallized from 10 ml of diethyl ether
10. customdried under vacuum at 50° C.

ORD record

ord-164a2a2e920f47b6b4f623242601d707

Source dataset

uspto-grants-2001_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06200989B1