Sodium Iodide → rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide

HRID 1109174Notes

Reaction equation

HRID 1109174 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.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].Br[CH2:25][CH2:26][CH2:27][CH2:28][N:29]1[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]2[C:30]1=[O:39]>CC(CC)=O.O>[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][N:11]3[CH2:25][CH2:26][CH2:27][CH2:28][N:29]3[C:33](=[O:34])[C:32]4=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]4[C:30]3=[O:39])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 93575N-(4-Bromobutyl)phthalimideHCID 101650127rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole

Product 1

HCID 131718425rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimideYield 103.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A solution of 1.00 g (0.005 mol) of rac-cis-2,3,3a,4,5,9b-hexahydro-6-methoxy-1H-benzo[e]indole in 60 ml of ethyl methyl ketone was treated with 0.86 g (0.006 mol) of potassium carbonate, 0.29 g (0.002 mol) of sodium iodide and 1.40 g (0.005 mol) of N-(4-bromobutyl)phthalimide. The mixture was boiled under reflux for 24 hours and, after cooling, treated with water. The mixture was extracted with ethyl acetate, the extracts were dried with sodium sulphate and the solvent was distilled off in a vacuum. Chromatography over silica gel with methylene chloride/methanol 20:1 gave 2.10 g (quant.) of crude rac-cis-N-[4-(1,2,3a,4,5,9b-hexahydro-6-methoxy-3H-benzo[e]indol-3-yl)butyl]phthalimide as pale yellow crystals. A small sample was recrystallized from ethyl acetate/ether and then exhibited a m.p. of 103°-105°.

Workup

  1. temperatureunder reflux for 24 hours
  2. temperatureafter cooling
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried with sodium sulphate
  5. distillationthe solvent was distilled off in a vacuum

Sources & evidence

ORD record
ord-1ac00a2ec62e4b1e8bd581453b829125
Source dataset
uspto-grants-1994_06
Patent number
US05318967

Reaction notes

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