Acetone → 6-[2-(isopropylamino)ethyl]-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

HRID 514778Notes

Reaction equation

HRID 514778 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17](=[O:20])[CH2:18][CH2:19][C:12]=3[C:11]=2[C:10]2[C:9]3[CH2:21][CH2:22][C:23](=[O:24])[C:8]=3[CH:7]=[CH:6][C:5]1=2.[CH3:25][C:26]([CH3:28])=O.C([O-])(O)=O.[Na+].Cl>C(Cl)Cl.CO.O1CCOCC1.C(Cl)(Cl)Cl.CO>[CH:26]([NH:1][CH2:2][CH2:3][N:4]1[C:16]2[CH:15]=[CH:14][C:13]3[C:17](=[O:20])[CH2:18][CH2:19][C:12]=3[C:11]=2[C:10]2[C:9]3[CH2:21][CH2:22][C:23](=[O:24])[C:8]=3[CH:7]=[CH:6][C:5]1=2)([CH3:28])[CH3:25]

Participants

9

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 453811166-(2-aminoethyl)-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

Product 1

HCID 445191266-[2-(isopropylamino)ethyl]-10,11-dihydro-1H-dicyclopenta[c,g]carbazole-3,9(2H,6H)-dione

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent3×HCID 312751,4-DioxaneSolventHCID 21584188Chloroform methanolSolvent

Procedure

Crude compound 59 (1.69 g) was suspended in CH2Cl2 (200 mL). Then acetone (4 mL) and STAB (3.4 g) were added. The mixture was stirred for 24 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1), then poured into an aqueous NaHCO3 solution. Then, another portion of CH2Cl2 and MeOH was added. The organic layer was separated, evaporated, washed with MeCN and ether. Yield of Example 8: 0.759 g. For the preparation of hydrochloride, the isolated product was suspended in a mixture of CH2Cl2 and MeOH, then a solution of HCl in dioxane was added. The resulting mixture was evaporated to dryness, and ethanol was added to the residue. The ethanolic solution was refluxed and cooled, and the precipitate was filtered. Yield of compound Example 8 hydrochloride: 0.684 g. 1H-NMR (DMSO-D6) spectrum: δ 1.24 (6H, d, J=6.6 Hz); 2.77-2.79 (4H, m); 3.34-3.43 (3H, m); 3.81-3.84 (4H, m); 4.91 (2H, t, J=7.3 Hz); 7.83 (2H, d, J=8.6 Hz); 7.91 (2H, d, J=8.6 Hz); 9.11 (2H, br. s). ELSD: 100%, ESI-MS: m/z 360 [M+H].+

Workup

  1. customThe organic layer was separated
  2. customevaporated
  3. washwashed with MeCN and ether
  4. customFor the preparation of hydrochloride
  5. customThe resulting mixture was evaporated to dryness, and ethanol
  6. additionwas added to the residue
  7. temperatureThe ethanolic solution was refluxed
  8. temperaturecooled
  9. filtrationthe precipitate was filtered

Sources & evidence

ORD record
ord-0a6104f2889d4779992b088f2be66af3
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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