Water → HCID 20227275, compound

To a stirred solution of 8.4 g of 5-bromo-3-(3-dimethylaminopropyl)-spiro[benzofuran-2(3H),1'-cycloheptane] hydrochloride in 57 ml of methanol, at room temperature under nitrogen, was added 7.44 g of N-bromosuccinimide. All solid dissolved as the pot temperature rose to 37° C. After stirring overnight at room temperature under nitrogen, the mixture was poured into 250 ml of water, made basic by addition of 100 ml of 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate (2×250 ml). The combined organic extracts were washed with water (100 ml) and saturated sodium chloride solution (100 ml) and dried overnight over anhydrous sodium sulfate. Filtration and concentration in vacuo afforded a mixture of oil and solid. This material was taken up in 100 ml of ethyl acetate and gravity-filtered, and the filtrate was stirred and treated dropwise with 10 ml of hydrogen chloride-saturated ether solution. The precipitated salt was filtered off, washed with ether and dried in vacuo to afford 2.85 g of a solid, m.p. sinters 200°, 202°-204° C. A second crop which had precipitated out of the filtrate was filtered off and washed with ether to afford, without drying, an additional 1.2 g of a solid, m.p. sinters 200°, 201°-202.5° C. The two crops of crude salt were combined and dissolved in 50 ml of absolute ethanol and gravity-filtered, and the filtrate was treated dropwise with ether (350 ml) with stirring. After stirring the mixture for a short period of time, the recrystallized solid was filtered off, washed with ether and dried to afford 2.2 g of a solid, m.p. 203.5°-206° C.

1. dissolutionAll solid dissolved as the pot temperature
2. customrose to 37° C
3. extractionextracted with ethyl acetate (2×250 ml)
4. washThe combined organic extracts were washed with water (100 ml) and saturated sodium chloride solution (100 ml)
5. dry with materialdried overnight over anhydrous sodium sulfate
6. filtrationFiltration and concentration in vacuo
7. customafforded
8. additiona mixture of oil and solid
9. filtrationgravity-filtered
10. stirringthe filtrate was stirred
11. additiontreated dropwise with 10 ml of hydrogen chloride-saturated ether solution
12. filtrationThe precipitated salt was filtered off
13. washwashed with ether
14. customdried in vacuo

ORD record

ord-45d16b7705c04ef3913d1ae5a6e04158

Source dataset

uspto-grants-1986_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04623657