Fumaric Acid → HCID 18462081, compound

HRID 2303954Notes

Reaction equation

HRID 2303954 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][C:7]3=[C:6]([CH:15]=[C:16]([N+:18]([O-])=O)[CH3:17])[C:5]=2[CH:4]=1.[C:21]([CH:24]([CH:26]([C:28]([O-:30])=[O:29])O)O)([O-:23])=[O:22].[Na+].[K+].C(O)(=O)/C=C/C(O)=O>CC(O)C>[C:28]([OH:30])(=[O:29])/[CH:26]=[CH:24]/[C:21]([OH:23])=[O:22].[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]3[CH2:12][CH2:13][CH2:14][C:7]3=[C:6]([CH2:15][CH:16]([NH2:18])[CH3:17])[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 444972Fumaric AcidHCID 9855836Potassium sodium tartarateHCID 69849776HCID 69849776, compound

Product 1

HCID 18462081HCID 18462081, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
0 °C

Procedure

(RS)-1-(7-Methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-propylamine fumarate was prepared from 1-(7-methoxy-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl)-2-nitro-1-propene according to hthe method described in Example 1 with the following modifications: the reaction mixture was heated under reflux for 4 h, cooled to 0° C. and aqueous potassium sodium tartrate solution (50 mL) was added slowly. The mixture was stirred for 30 min, filtered through a pad of kieselguhr and the filtrate was extracted with dichloromethane (3×30 mL). The combined organic extracts were washed (water, brine), dried (sodium sulfate) and concentrated in vacuo. The concentrate was dissolved in 2-propanol (1 mL) and added to a solution of fumaric acid (0.17 g, 1.5 mmol) in 2-propanol (20 mL) at 50° C. The solution was cooled to 0° C. and filtered. The filter-cake was washed (2-propanol, ether) and dried to give the title compound as a white solid (0.22 g, 42%): mp 194-196° C.; Found: C, 63.27; H, 6.80; N, 7.69%. C19H24N2O5 requires: C, 63.32; H, 6.71; N, 7.77%.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 4 h
  3. filtrationfiltered through a pad of kieselguhr
  4. extractionthe filtrate was extracted with dichloromethane (3×30 mL)
  5. washThe combined organic extracts were washed (water, brine)
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. dissolutionThe concentrate was dissolved in 2-propanol (1 mL)
  9. temperatureThe solution was cooled to 0° C.
  10. filtrationfiltered
  11. washThe filter-cake was washed (2-propanol, ether)
  12. customdried

Sources & evidence

ORD record
ord-0b50222299a3497a95fb3dce06453b10
Source dataset
uspto-grants-2002_08
Patent number
US06433175B1

Reaction notes

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