Sodium Iodide → 1-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester

Temperature

65 °C

A mixture of 12-(3-bromo-1-propylidene)-12H-dibenzo[d,g][1,3]dioxocine (4.0 g, 12 mmol, prepared as described in example 1), 4-piperidinecarboxylic acid ethyl ester (1.9 g, 12 mmol), anhydrous potassium carbonate (5.0 g) and sodium iodide (0.2 g) in N,N-dimethylformamide (40 ml) was heated at 60-70° C. for 5 h. After cooling, the inorganic salts were filtered off and washed with benzene (40 ml), and the filtrate was diluted with additional benzene (120 ml). The benzene solution was washed with water (3×50 ml), dried over MgSO4 and evaporated in vacuo. The oily residue (4.8 g) was purified by chromatography on silica gel using a mixture of benzene and ethyl acetate as eluent to give 1-(3-(12H-dibenzo[d,g][1,3]dioxocin-12-ylidene)-1-propyl)-4-piperidinecarboxylic acid ethyl ester as an oil (2.3 g, 47%).

1. temperatureAfter cooling
2. filtrationthe inorganic salts were filtered off
3. washwashed with benzene (40 ml)
4. additionthe filtrate was diluted with additional benzene (120 ml)
5. washThe benzene solution was washed with water (3×50 ml)
6. dry with materialdried over MgSO4
7. customevaporated in vacuo
8. customThe oily residue (4.8 g) was purified by chromatography on silica gel using
9. additiona mixture of benzene and ethyl acetate as eluent

ORD record

ord-c0b1cf4c6d80497fb27bdbbb56bcb9bb

Source dataset

uspto-grants-1999_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05917047