1-Chloroethyl chloroformate → HCID 23402467, compound

Temperature

80 °C

A solution of 0.30 gm (1.01 mMol) 1-benzyl-2(S)-(benzyloxymethyl)piperazine in 20 mL 1,2-dichloroethane was cooled to 0° C. To this solution were added 1.09 mL (10.1 mMol) 1-chloroethyl chloroformate and the resulting mixture was heated at 80° C. for 4 hours. The reaction mixture was then cooled again to 0° C. and an additional 2.18 mL (20.2 mMol) 1-chloroethyl chloroformate were added. The reaction mixture was heated at reflux overnight and was then concentrated under reduced pressure. The residue was dissolved in 40 mL methanol and heated at reflux for 2 hours. The mixture was concentrated under reduced pressure and the residue subjected to silica gel chromatography, eluting with dichloromethane containing 0–10% methanol and 0.1% ammonium hydroxide. Fractions containing the desired product were combined and concentrated under reduced pressure to provide 0.17 gm (81%) of the title compound.

1. temperatureThe reaction mixture was then cooled again to 0° C.
2. temperatureThe reaction mixture was heated
3. temperatureat reflux overnight
4. concentrationwas then concentrated under reduced pressure
5. dissolutionThe residue was dissolved in 40 mL methanol
6. temperatureheated
7. temperatureat reflux for 2 hours
8. concentrationThe mixture was concentrated under reduced pressure
9. washeluting with dichloromethane containing 0–10% methanol and 0.1% ammonium hydroxide
10. additionFractions containing the desired product
11. concentrationconcentrated under reduced pressure

ORD record

ord-58c008cc7e4a41aaa3b16c6b78e52f10

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967201B1