Sodium hydride → 6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

HRID 1615032Notes

Reaction equation

HRID 1615032 reaction equation
[CH2:1]1[C:16]2[C:15]3[C:14]4[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=4[NH:8][C:7]=3[CH:6]=[CH:5][C:4]=2[C:3](=[O:17])[CH2:2]1.[H-].[Na+].Cl.Cl[CH2:22][CH2:23][CH:24]1[CH2:28][CH2:27][CH2:26][N:25]1[CH3:29].C(Cl)(Cl)Cl.CO>C(Cl)Cl.O>[CH3:29][N:25]1[CH2:26][CH2:27][CH2:28][CH:24]1[CH2:23][CH2:22][N:8]1[C:7]2[CH:6]=[CH:5][C:4]3[C:3](=[O:17])[CH2:2][CH2:1][C:16]=3[C:15]=2[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 3017050Pyrrolidine, 2-(2-chloroethyl)-1-methyl-, hydrochloride (1:1)HCID 21584188Chloroform methanolHCID 585448961,6-Dihydrocyclopenta[c]carbazol-3(2H)-one

Product 1

HCID 585449036-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Carbazole 46 (0.4 g, 1.81 mmol) was dissolved in CH2Cl2 (7 mL), then NaH (0.22 g, 5.50 mmol) was added. The mixture was stirred at room temperature for 5-10 min, and 2-(2-chloroethyl)-1-methylpyrrolidine hydrochloride (0.4 g, 2.17 mmol) was added. The mixture was heated to 60° C. and kept at this temperature for 4 h (TLC monitoring, eluent: CHCl3-MeOH, 9:1). The resulting mixture was poured into water. The product was extracted with ethyl acetate, dried over Na2SO4, and evaporated. The residue was triturated with ether. The precipitate was filtered off. Yield of 65: 0.365 g (61%)—S-isomer and 0.336 g (55%)—R-isomer.

Workup

  1. temperatureThe mixture was heated to 60° C.
  2. waitkept at this temperature for 4 h
  3. extractionThe product was extracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customThe residue was triturated with ether
  7. filtrationThe precipitate was filtered off

Sources & evidence

ORD record
ord-fba698b804b14d39a1478d026d78780a
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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