Hydrochloric Acid → HCID 70545911, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of trans-3,4-dichloro-N-methyl-N-[8-(1-pyrrolidinyl)-1,4-dioxaspiro[4.5]dec-7-yl]benzeneacetamide (4.5 g, 0.01 mmole) prepared by procedures described above, and 100 ml of 3 N HCl solution was stirred under N2 atmosphere while 150 ml of acetone was added. The mixture was stirred at 58° C. for one hour and cooled to room temperature. Removed the acetone in vacuo and neutralized the mixture by addition of solid NaHCO3 with intermittant cooling of the mixture in a dry ice-acetone bath. Extracted the aqueous layer with CHCl3 ; the CHCl3 extracts were dried (Na2SO4) and concentrated in vacuo to a pale yellow oil (5 g). Dissolved the oil in CHCl3 and treated the solution with ethereal HCl. Separated the solvent from a pale yellow gum and dissolved the gum in CHCl3. Diluted the CHCl3 solution with ether and refrigerated overnight. Filtered the white solid which deposited and dried in vacuo at 40° C. to give a total of 4.95 g of the titled cyclohexanone. Mass spectrum m/e 382/384 (M+, chlorine isotopic peaks). IR NH (2600, 2480), C=O (ketone) 1725, C=O (amide) 1645 cm-1 and nmr spectra were consistent with the structure assignment.

Provenance & Evidence