Hydrochloric Acid → HCID 70545911, compound

HRID 2198954Notes

Reaction equation

HRID 2198954 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:28])[C@H:13]2[C@H:22]([N:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH2:21][CH2:20][C:15]3(OCC[O:16]3)[CH2:14]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>CC(C)=O>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:28])[C@@H:13]2[CH2:14][C:15](=[O:16])[CH2:20][CH2:21][C@H:22]2[N:23]2[CH2:24][CH2:25][CH2:26][CH2:27]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 13062445HCID 13062445, compound

Product 1

HCID 70545911HCID 70545911, compoundYield 235,841.703%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
58 °C

Procedure

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.

Workup

  1. additionwas added
  2. temperaturecooled to room temperature
  3. customRemoved the acetone in vacuo
  4. additionby addition of solid NaHCO3
  5. temperaturewith intermittant cooling of the mixture in a dry ice-acetone bath
  6. extractionExtracted the aqueous layer with CHCl3
  7. dry with materialthe CHCl3 extracts were dried (Na2SO4)
  8. concentrationconcentrated in vacuo to a pale yellow oil (5 g)
  9. dissolutionDissolved the oil in CHCl3
  10. additiontreated the solution with ethereal HCl
  11. customSeparated the solvent from a pale yellow gum
  12. dissolutiondissolved the gum in CHCl3
  13. additionDiluted the CHCl3 solution with ether and refrigerated overnight
  14. filtrationFiltered the white solid which
  15. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-678da07f21714066b9db82545a06bae4
Source dataset
uspto-grants-1982_11
Patent number
US04360531

Reaction notes

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