Sodium Iodide → HCID 131723338, compound

Temperature

0 °C

3.48 g (42.7 mmole) of freshly dried dimethylamine hydrochloride were added while stirring to 94 ml (94 mmole) of sodium iodide solution (1 M in acetonitrile), cooled to 0° C. with an ice bath, followed by the dropwise addition of 12 ml (85.4 mmole) of triethylamine and 12 ml (94 mmole) of chlorotrimethylsilane, and the whole was stirred for a further hour at RT. 4.8 ml (42.7 mmole) of 3-chlorobenzaldehyde were added while cooling with ice, and the whole was stirred for a further hour at RT. The reaction mixture was cooled again to 0° C. with an ice bath, 6.9 ml (42.7 mmole) of 1-(pyrrolidino)-1-cyclohexene were added, and the whole was stirred for a further two hours at RT. The reaction mixture was worked up by adding 60 ml of semi-concentrated hydrochloric acid, stirred for 10 minutes, washed twice with 60 ml of ether each time, and adjusted in the alkaline range (pH ca. 9) with 150 ml of dilute ammonia solution (5 vol. %). The reaction mixture was extracted three times with 60 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 8.97 g of crude base (79.1% of theory) were obtained, from which a hydrochloride was precipitated according to Example 1 (3rd stage) with chlorotrimethylsilane/water in 2-butanone. The base was freed from the hydrochloride with 90 ml of water and 15 ml of ammonia solution (25 vol. %), extracted three times with 50 ml of ether each time, and the combined organic extracts were dried over sodium sulfate, filtered, and concentrated by evaporation on a rotary evaporator without heating (500 to 10 mbar). 7.05 g of crude base (62.1% of theory) were obtained, from which 7.38 g of the hydrochloride of 2-[(3-chlorophenyl)(dimethylaminomethyl]cyclohexanone (57.2% of theory) were obtained according to the procedure described in Example 1 (2nd stage) with chlorotrimethylsilane/water in 2-butanone.

1. temperaturewhile cooling with ice
2. stirringthe whole was stirred for a further hour at RT
3. temperatureThe reaction mixture was cooled again to 0° C. with an ice bath
4. stirringthe whole was stirred for a further two hours at RT
5. stirringstirred for 10 minutes
6. washwashed twice with 60 ml of ether each time
7. extractionThe reaction mixture was extracted three times with 60 ml of ether each time
8. dry with materialthe combined organic extracts were dried over sodium sulfate
9. filtrationfiltered
10. concentrationconcentrated by evaporation on a rotary evaporator
11. temperaturewithout heating (500 to 10 mbar)
12. custom8.97 g of crude base (79.1% of theory) were obtained, from which a hydrochloride
13. customwas precipitated
14. extractionextracted three times with 50 ml of ether each time
15. dry with materialthe combined organic extracts were dried over sodium sulfate
16. filtrationfiltered
17. concentrationconcentrated by evaporation on a rotary evaporator
18. temperaturewithout heating (500 to 10 mbar)

ORD record

ord-1864cb719cf14ca591c086dc6106ccf4

Source dataset

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06410790B1