Acetyl chloride → cetyl-6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3 (2H)-one

HRID 514784Notes

Reaction equation

HRID 514784 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:7][CH2:8][N:9]1[C:21]2[CH:20]=[CH:19][C:18]3[C:22](=[O:25])[CH2:23][CH2:24][C:17]=3[C:16]=2[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2.[Al+3].[Cl-].[Cl-].[Cl-].[C:30](Cl)([CH3:32])=O.C([O-])(O)=O.[Na+]>C1([N+]([O-])=O)C=CC=CC=1.O>[CH2:22]([CH:24]1[C:17]2[C:16]3[C:15]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[N:9]([CH2:8][CH2:7][CH:3]4[CH2:4][CH2:5][CH2:6][N:2]4[CH3:1])[C:21]=3[CH:20]=[CH:19][C:18]=2[C:22](=[O:25])[CH2:23]1)[CH2:23][CH2:24][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:16][CH2:15][CH2:10][CH2:11][CH2:12][CH2:13][CH2:30][CH3:32]

Participants

7

Reactant 4

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 6451240Aluminum(III) ChlorideHCID 585449036-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3(2H)-one

Product 1

HCID 131733294cetyl-6-[2-(1-methylpyrrolidin-2-yl)ethyl]-1,6-dihydrocyclopenta[c]carbazol-3 (2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 7416NitrobenzeneSolvent

Procedure

Compound 65 (0.336 g, 1.00 mmol) was dissolved in PhNO2 (7 mL). The solution was cooled down in an ice bath. Then, AlCl3 (0.67 g, 5.02 mmol) and after that, AcCl (0.36 mL, 5.04 mmol) were added. The resulting mixture was kept for 40 min (LC/MS monitoring), diluted with water, neutralized with aqueous NaHCO3 solution, extracted with CHCl3, and evaporated. The product was purified on a short thick column, eluent: 100:0→90:10. Yield of product: 0.307 g (82%) (R); S-isomer was obtained similarly (77%).

Workup

  1. temperatureThe solution was cooled down in an ice bath
  2. extractionextracted with CHCl3
  3. customevaporated
  4. customThe product was purified on a short thick column, eluent
  5. customS-isomer was obtained similarly (77%)

Sources & evidence

ORD record
ord-778fe26d176f437784e3395bba33489d
Source dataset
uspto-grants-2015_08
Patent number
US09108916B2

Reaction notes

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