Phosgene → HCID 22063415, compound

A round bottom flask containing phosgene (20% wt in toluene, 3.16 mL) and dichloromethane (10 mL) was cooled with an ice bath. A solution of N-ethyl-N-isopropylpropan-2-amine (1.393 mL) and piperidine-4-carbonitrile (0.441 g) in dichloromethane (5 mL) was added via a syringe dropwise. The mixture was stirred at room temperature overnight and then concentrated to dryness. The residue was dissolved in methanol (10 mL) and 2 mL of 7 N NH3 in methanol. The mixture was stirred at 50° C. overnight. The mixture was concentrated and the residual solid was mixed with brine (5 mL) and extracted with ethyl acetate (8×25 mL). The organic solution was dried (MgSO4), filtered and concentrated. The crude material was purified on a silica gel column eluting with 5-10% methanol in CH2Cl2.

1. temperaturewas cooled with an ice bath
2. concentrationconcentrated to dryness
3. dissolutionThe residue was dissolved in methanol (10 mL)
4. stirringThe mixture was stirred at 50° C. overnight
5. concentrationThe mixture was concentrated
6. additionthe residual solid was mixed with brine (5 mL)
7. extractionextracted with ethyl acetate (8×25 mL)
8. dry with materialThe organic solution was dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customThe crude material was purified on a silica gel column
12. washeluting with 5-10% methanol in CH2Cl2

ORD record

ord-232fb6d7fc81417abb2063fb2d1d7424

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08557983B2