Triethylamine → HCID 21833725, compound

A stirred solution of 2,3-dihydro-1'-methylspiro[4H-benzopyran-4,4'-piperidine] (D101, 1.0 g, 0.0046 mole) and diisopropylethylamine (1.2 ml, 0.0070 mole) in dichloroethane (20 ml) was treated with 1-chloroethyl chloroformate (0.64 ml, 0.0060 mole) and kept at room temp. for 1 h followed by 20 mins at reflux. The solution was then concentrated in vacuo and the residue treated with methanol (20 ml) and heated under reflux for 2 h. The reaction mixture was concentrated in vacuo to leave a beige solid, which was dissolved in dichloromethane (50 ml) and THF (10 ml) and treated with triethylamine (0.84 ml, 0.0060 mole) followed by ethyl chloroformate (0.44 ml, 0.0046 mole). The solution was stirred at room temperature for 2 h, then treated with 10% Na2CO3 solution (20 ml) and extracted with dichloromethane (2×40 ml). The combined extract was dried (Na2SO4) and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 1:1 ether/60-80 petrol to afford the title compound as a yellow oil (1.3 g, 100%).

1. waitfollowed by 20 mins
2. temperatureat reflux
3. concentrationThe solution was then concentrated in vacuo
4. additionthe residue treated with methanol (20 ml)
5. temperatureheated
6. temperatureunder reflux for 2 h
7. concentrationThe reaction mixture was concentrated in vacuo
8. customto leave a beige solid, which
9. extractionextracted with dichloromethane (2×40 ml)
10. extractionThe combined extract
11. dry with materialwas dried (Na2SO4)
12. concentrationconcentrated in vacuo
13. customThe residue was chromatographed on silica gel eluting with 1:1 ether/60-80 petrol

ORD record

ord-2e2d3d30deb84c06a4371a712f1563f7

Source dataset

uspto-grants-1999_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05972951