Phosgene → HCID 15053374, compound

To a stirred suspension of 10 g (0.072 mole) of finely ground potassium carbonate in 90 ml of methylene chloride was added 32 ml (0.062 mole) of 2M phosgene in benzene. The mixture was stirred for 15 min and 8 g (0.031 mole) of 1-(1-phenylethyl)-3-(2-pyridyloxy)azetidine in 50 ml of methylene chloride was added. The mixture was stirred at 25° C. for 2 hr and concentrated on a rotary evaporator at 25° C./30 mm and the residue was treated with 100 ml of tetrahydrofuran. The stirred mixture was cooled with an ice bath and treated dropwise with 4 g (0.07 mole) of allyl amine. After stirring 30 min at 25° C., the material was partitioned between water and methylene chloride. The methylene chloride was dried and concentrated. The residue was chromatographed on a Waters® PREP-500 HPLC using a silica column and eluting with 50% ethylacetate-hexane. The product was crystallized twice from isopropyl ether. Yield of title compound was 1.5 g (21%), m.p. 72°-76° C.

1. stirringThe mixture was stirred at 25° C. for 2 hr
2. concentrationconcentrated on a rotary evaporator at 25° C./30 mm
3. additionthe residue was treated with 100 ml of tetrahydrofuran
4. temperatureThe stirred mixture was cooled with an ice bath
5. stirringAfter stirring 30 min at 25° C.
6. customthe material was partitioned between water and methylene chloride
7. dry with materialThe methylene chloride was dried
8. concentrationconcentrated
9. customThe residue was chromatographed on a Waters®
10. washeluting with 50% ethylacetate-hexane
11. customThe product was crystallized twice from isopropyl ether

ORD record

ord-51db79760ce648d88abd54a96ba76e09

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05183902