Hydrochloric Acid → HCID 13062448, compound

HRID 2198953Notes

Reaction equation

HRID 2198953 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:28])[C@@H:13]2[CH2:22][CH2:21][C:16]3(OCC[O:17]3)[CH2:15][C@H:14]2[N:23]2[CH2:27][CH2:26][CH2:25][CH2:24]2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([N:12]([CH3:28])[C@@H:13]2[CH2:22][CH2:21][C:16](=[O:17])[CH2:15][C@H:14]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 13062442HCID 13062442, compound

Product 1

HCID 13062448HCID 13062448, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of trans-3,4-dichloro-N-methyl-N-[7-(1-pyrrolidinyl)-1,4-dioxaspiro[4.5]dec-8-yl]benzeneacetamide (12.3 g, 0.029 mol) from Example 1, 3 N HCl solution (288 ml), and 432 ml of acetone was stirred at 60° C. under N2 atmosphere for one hour. Acetone was removed on a rotary evaporator and the mixture was extracted with chloroform. The chloro-form extracts were dried (Na2SO4), concentrated in vacuo and diluted with ether. Refrigeration overnight gave white crystals which were dried at 60° C. in vacuo for two days to give 10.5 g (87%) of the titled compound, mp 148.0°-148.9° C. The mass spectrum indicated ion fragments at m/e 382/384 (M+, chlorine isotopic peaks). The ir and nmr spectra were consistent with the structure assignment.

Workup

  1. customAcetone was removed on a rotary evaporator
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialThe chloro-form extracts were dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. additiondiluted with ether
  6. customRefrigeration overnight gave white crystals which
  7. customwere dried at 60° C. in vacuo for two days

Sources & evidence

ORD record
ord-5363d821799249ac8111317fa0956901
Source dataset
uspto-grants-1982_11
Patent number
US04360531

Reaction notes

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