Phenethyl bromide → 1,2,3,4,5,6-Hexahydro-3,9-dimethyl-6-phenethylazepino[4,5-b]indole

HRID 1481412Notes

Reaction equation

HRID 1481412 reaction equation
[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[NH:6][C:5]=2[CH2:4][CH2:3]1.N1CCC[C@H]1C(O)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].Br[CH2:34][CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>[Cu](I)I.O.CN(C=O)C>[CH3:1][N:2]1[CH2:15][CH2:14][C:13]2[C:12]3[CH:11]=[C:10]([CH3:16])[CH:9]=[CH:8][C:7]=3[N:6]([CH2:34][CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:5]=2[CH2:4][CH2:3]1

Participants

8

Reactant 4

HCID 7666Phenethyl bromideHCID 62657Potassium Phosphate, TribasicHCID 145742L-ProlineHCID 685600921,2,3,4,5,6-Hexahydro-3,9-dimethylazepino[4,5-b]indole

Product 1

HCID 593683711,2,3,4,5,6-Hexahydro-3,9-dimethyl-6-phenethylazepino[4,5-b]indole

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

The title compound was prepared by following general procedure 4. 3,9-Dimethyl-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole (214 mg, 1.0 mmol) was taken with copper iodide (19 mg, 0.1 mmol), L-proline (23 mg, 0.2 mmol), potassium phosphate tribasic (426 mg, 2.0 mmol) and (2-bromoethyl)benzene (185 mg, 1 mmol) and DMF was added, the reaction was stirred at 90° C. under argon atmosphere for 12 h. The reaction was monitored by LCMS. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was washed with water, dried over sodium sulfate and concentrated under vacuum. The crude so obtained was purified by column chromatography (silica gel 100-200 mesh) (gradient 5% MeOH:DCM). The pure product was converted to oxalate salt using oxalic acid and THF.

Workup

  1. additionwas added
  2. additionwas added
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe crude so obtained
  8. customwas purified by column chromatography (silica gel 100-200 mesh) (gradient 5% MeOH:DCM)

Sources & evidence

ORD record
ord-140a5d9478324fa6af24d5ce6dd16853
Source dataset
uspto-grants-2016_08
Patent number
US09409910B2

Reaction notes

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