Triethylamine → HCID 19610943, compound

HRID 1602332Notes

Reaction equation

HRID 1602332 reaction equation
[ClH:1].Cl.[N:3]12[CH2:10][CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([NH:11][NH2:12])[CH2:4]2.[CH3:13][N:14](C=NC=[N+](C)C)[CH3:15].[Cl-].CCN(CC)CC.C(=O)([O-])[O-].[K+].[K+].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl.CO.CC(C)=O.C(OCC)C>C(Cl)(Cl)Cl>[ClH:1].[ClH:1].[N:11]1([CH:5]2[CH:6]3[CH2:9][CH2:10][N:3]([CH2:8][CH2:7]3)[CH2:4]2)[CH:15]=[N:14][CH:13]=[N:12]1

Participants

8

Reactant 6

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 11008255Gold's ReagentHCID 18412823HCID 18412823, compoundHCID 19610903HCID 19610903, compound

Product 1

HCID 19610943HCID 19610943, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3-Quinuclidyl-hydrazine dihydrochloride salt (D5) (200 mg, 1.0 mmol) and Gold's reagent ([3-(dimethylamino)-2-azaprop-2-en-1-ylidene]-dimethylammonium chloride) (153 mg, 1.0 mmol) were dissolved in dry CHCl3 (20 ml) under N2 and dry Et3N (0.28 ml, 2.0 mmol) was added. The solution was heated at reflux under nitrogen for 2.5 h. The solution was cooled, saturated aqueous potassium carbonate was added and the organic layer separated. The aqueous layer was extracted with CHCl3 (2×100 ml), the organic extracts were dried (Na2SO4), filtered and were evaporated to dryness under reduced pressure. The resulting orange/yellow oil was purified by column chromatography (basic alumina eluting with 2% MeOH/EtOAc). The resulting clear oil was recrystallised as the dihydrochloride salt from methanol/acetone/diethyl ether (45 mg, 0.18 mmol, 18%), m.p. 187-190° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat reflux under nitrogen for 2.5 h
  3. temperatureThe solution was cooled
  4. customthe organic layer separated
  5. extractionThe aqueous layer was extracted with CHCl3 (2×100 ml)
  6. dry with materialthe organic extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. customwere evaporated to dryness under reduced pressure
  9. customThe resulting orange/yellow oil was purified by column chromatography (basic alumina eluting with 2% MeOH/EtOAc)

Sources & evidence

ORD record
ord-6282ebb182cc45c2860f98955a199a62
Source dataset
uspto-grants-1999_11
Patent number
US05981545

Reaction notes

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