Potassium Carbonate → HCID 15745003, compound

HRID 1648285Notes

Reaction equation

HRID 1648285 reaction equation
[CH2:1]([NH:4][CH:5]1[CH2:14][C:13]2=[CH:15][CH:16]=[CH:17][C:11]3=[C:12]2[N:7]([CH2:8][CH2:9][CH2:10]3)[CH2:6]1)[CH2:2][CH3:3].[CH2:18](I)[CH2:19][CH3:20].C(=O)([O-])[O-].[K+].[K+].[OH-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([N:4]([CH2:18][CH2:19][CH3:20])[CH:5]1[CH2:14][C:13]2=[CH:15][CH:16]=[CH:17][C:11]3=[C:12]2[N:7]([CH2:8][CH2:9][CH2:10]3)[CH2:6]1)[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 11430Potassium Carbonate2×HCID 14798Sodium HydroxideHCID 336431-Iodopropane2×HCID 15745002HCID 15745002, compound

Product 1

HCID 15745003HCID 15745003, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,3,6,7-tetrahydro-N-propyl-1H,5H-benzo(ij)quinolizin-2-amine (2.33 g, 0.01 tool), propyl iodide (5.16 g, 0.03 tool) and anhydrous potassium carbonate (3 g, 0.02 tool) in dimethylformamide (75 mL) was stirred for 5 hours at 90° C. At this time additional propyl iodide (1.72 g, 0.01 mol) and potassium carbonate (0.5 g, 0.0036 mol) were added and the reaction was continued for an additional 2 hours. The reaction was cooled, filtered to remove inorganic material, and the solvent was removed under reduced pressure. The product was partitioned between ethyl acetate (800 mL) and 4N sodium hydroxide (20 mL, 0.08 mol), the organic layer concentrated, filtered, and chromatographed on silica gel in 5-30% ethyl acetate:hexane to give 2.19 g of 2,3,6,7-tetrahydro-N,N-dipropyl-1H,5H-benzo(ij)quinolizin-2-amine.

Workup

  1. waitthe reaction was continued for an additional 2 hours
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customto remove inorganic material
  5. customthe solvent was removed under reduced pressure
  6. concentrationthe organic layer concentrated
  7. filtrationfiltered
  8. customchromatographed on silica gel in 5-30% ethyl acetate

Sources & evidence

ORD record
ord-591497503df14e2286c02fe00b8b16d7
Source dataset
uspto-grants-1995_07
Patent number
US05436240

Reaction notes

Loading…