Sodium Iodide → rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole

HRID 1109171Notes

Reaction equation

HRID 1109171 reaction equation
[CH3:1][O:2][C:3]1[C:15]2[CH2:14][CH2:13][C@H:12]3[C@H:8]([CH2:9][CH2:10][NH:11]3)[C:7]=2[CH:6]=[CH:5][CH:4]=1.[CH:16]1([CH2:22][CH2:23]Br)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(CC)=O>[CH:16]1([CH2:22][CH2:23][N:11]2[C@@H:12]3[C@@H:8]([C:7]4[CH:6]=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[C:15]=4[CH2:14][CH2:13]3)[CH2:9][CH2:10]2)[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 15440(2-Bromoethyl)cyclohexaneHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718424rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indoleYield 43%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 24.1 g (0.12 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole, 28.3 g (0.15 mol) of 2-cyclohexylethyl bromide, 26.3 g (0.19 mol) of potassium carbonate and 6.22 g (0.04 mol) of sodium iodide in 550 ml of ethyl methyl ketone was boiled at reflux for 3 days. The solid was filtered off and the solvent was distilled in a vacuum. The residue was dissolved in ethyl acetate, whereupon the solution was washed with water and sodium chloride solution and concentrated. After chromatography over silica gel (ethyl acetate-methylene chloride 1:2) there were obtained 16.1 g (43%) of rac-cis-3-(2-cyclohexylethyl)-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benz[e]indole as a beige oil.

Workup

  1. temperatureat reflux for 3 days
  2. filtrationThe solid was filtered off
  3. distillationthe solvent was distilled in a vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate, whereupon the solution
  5. washwas washed with water and sodium chloride solution
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-acf6153cfae44ce6868cc4d94fe1f8d5
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

Loading…