Ammonia → HCID 19814746, compound

Temperature

80 °C

A stirred solution of 1-benzyl-3-(3-chloropropyl)-azetidine-3-carbonitrile (D1, 5.35 g, 0.022 mole) in methanol (75 ml) was treated cautiously with 18 concentrated sulphuric acid (15 ml) and then heated at 80° C. for 20 h. The solution was cooled in an ice bath and a further 12 ml of concentrated sulphuric acid added. The solution was heated at 80° C. for a further 9 hours, then allowed to cool, before pouring cautiously into ice/water (400 ml) with vigorous stirring. The aqueous mixture was basified by the addition of 0.88 ammonia solution, then extracted with ethyl acetate (2×200 ml). The combined extracts were dried (Na2SO4) and concentrated in vacuo to leave an orange oil, which was filtered through a basic alumina column eluting with ether. The colourless oil obtained was dissolved in ether (150 ml) and treated with a solution of oxalic acid (2.0 g, 0.022 mole) in methanol (10 ml). The title compound (D2) was filtered off as a white crystalline solid (7.25 g, 91%).

1. temperatureThe solution was cooled in an ice bath
2. temperatureThe solution was heated at 80° C. for a further 9 hours
3. temperatureto cool
4. extractionextracted with ethyl acetate (2×200 ml)
5. dry with materialThe combined extracts were dried (Na2SO4)
6. concentrationconcentrated in vacuo
7. customto leave an orange oil, which
8. filtrationwas filtered through a basic alumina column
9. washeluting with ether
10. customThe colourless oil obtained
11. filtrationThe title compound (D2) was filtered off as a white crystalline solid (7.25 g, 91%)

ORD record

ord-fdec225d0f4a4c128a78879d4c212560

Source dataset

uspto-grants-1991_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05043343