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 (1.385 mL) and piperidine-4-carbonitrile (0.441 g) in dichloromethane (5 mL) was added via a syringe dropwise. The mixture was stirred 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% and 10% methanol in CH2Cl2 to provide the title compound.

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% and 10% methanol in CH2Cl2

ORD record

ord-06a0246fd2944d389bcd780c9f1e0027

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08580794B2