Hydrochloric Acid → HCID 19972500, compound

HRID 2259909Notes

Reaction equation

HRID 2259909 reaction equation
[N:1]([CH2:4][CH2:5][O:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:44][O:45][C:46]1[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[C:47]=1[O:48][CH2:49][CH:50]=O.[ClH:58]>C1C=CC=CC=1>[ClH:58].[CH3:44][O:45][C:46]1[CH:55]=[CH:54][CH:53]=[C:52]([O:56][CH3:57])[C:47]=1[O:48][CH2:49][CH2:50][NH:1][CH2:4][CH2:5][O:6][C:7]1[C:16]2[O:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[C:13]([CH3:23])[C:12](=[O:24])[C:11]=2[CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 13383135HCID 13383135, compoundHCID 19972552HCID 19972552, compound

Product 1

HCID 19972500HCID 19972500, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 4.5 g of Intermediate XII, 3.7 g of triphenyl phosphine and 2.85 g of 2,6-dimethoxyphenoxy-acetaldehyde (prepared as per Nelson, W. L. et al., J. Med. Chem. 22: 1125, 1979) in 45 ml of benzene was stirred at 20°-25° C. for 18 hours and at reflux for 5 hours. The solvent was evaporated off in vacuo and the residue was dissolved in 80 ml of anhydrous methanol containing 3Å molecular sieves at 0° C. The mixture was stood for 1 hour at 0° C. and for 1 hour at 20°-25° C., and then poured into iced water and extracted with dichloromethane. The organic extracts were washed with water and dried on anhydrous sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel, eluting with dichloromethane:methanol (49:1). The base obtained was treated with ethanolic hydrogen chloride. After crystallization from ethanol, the title compound was obtained. Yield 40%, m.p. 200-°202° C.

Workup

  1. temperatureat reflux for 5 hours
  2. customThe solvent was evaporated off in vacuo
  3. dissolutionthe residue was dissolved in 80 ml of anhydrous methanol containing 3Å molecular sieves at 0° C
  4. waitThe mixture was stood for 1 hour at 0° C. and for 1 hour at 20°-25° C.
  5. additionpoured into iced water
  6. extractionextracted with dichloromethane
  7. washThe organic extracts were washed with water
  8. dry with materialdried on anhydrous sodium sulfate
  9. customThe solvent was removed in vacuo
  10. customthe residue was purified by flash chromatography on silica gel
  11. washeluting with dichloromethane:methanol (49:1)
  12. customThe base obtained
  13. customAfter crystallization from ethanol

Sources & evidence

ORD record
ord-42161be7176c4f45be13cfeadd8e1100
Source dataset
uspto-grants-1995_12
Patent number
US05474994

Reaction notes

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