Iodoethane → 3-(1-Acetylpiperidin-4-yl)-1-(1-ethyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanone

HRID 260297Notes

Reaction equation

HRID 260297 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:22]=[CH:21][C:20]3[NH:19][CH2:18][CH:17]4[CH2:23][CH2:24][CH2:25][C:15]=2[C:16]=34)=[O:13])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[CH2:26](I)[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[C:1]([N:4]1[CH2:5][CH2:6][CH:7]([CH2:10][CH2:11][C:12]([C:14]2[CH:22]=[CH:21][C:20]3[N:19]([CH2:26][CH3:27])[CH2:18][CH:17]4[CH2:23][CH2:24][CH2:25][C:15]=2[C:16]=34)=[O:13])[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 186210833-(1-Acetyl-4-piperidinyl)-1-(1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanone

Product 1

HCID 214767313-(1-Acetylpiperidin-4-yl)-1-(1-ethyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanoneYield 75.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 10 ml suspension of 1.0 g of 3-(1-acetylpiperidin-4-yl)-1-(1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanone, 2.3 g of ethyl iodide and 0.53 g of potassium carbonate in ethanol was stirred at 60° to 70° C. for 12 hours. After the solvent was distilled off under reduced pressure, water was added to the residue, after which the reaction product was extracted with dichloromethane. After the extract was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate) to yield 0.82 g of 3-(1-acetylpiperidin-4-yl)-1-(1-ethyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-6-yl)-1-propanone as a colorless oily substance.

Workup

  1. distillationAfter the solvent was distilled off under reduced pressure, water
  2. additionwas added to the residue
  3. extractionafter which the reaction product was extracted with dichloromethane
  4. dry with materialAfter the extract was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-fc254922a9e94c0eac2a6d7538efe6ba
Source dataset
uspto-grants-1996_06
Patent number
US05527800

Reaction notes

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