HCID 13062442, compound → HCID 13062448, compound

HRID 358354Notes

Reaction equation

HRID 358354 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]>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

3

Reactant 1

HCID 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) 3N 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 chloroform 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 chloroform 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-a52bbeafd9ad4f9db9bb017f61ed567e
Source dataset
uspto-grants-1984_08
Patent number
US04466977

Reaction notes

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