Allyl bromide → HCID 17896911, compound

HRID 1280331Notes

Reaction equation

HRID 1280331 reaction equation
[OH-].[Na+].[CH:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]1[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12][C:6]=1[NH:7]2.[CH2:19](Br)[CH:20]=[CH2:21]>[Br-].C[N+](C)(C)CCCCCCCCCCCCCCCC.C1C=CC=CC=1>[CH2:21]([N:7]1[C:8]2[C:4](=[CH:3][CH:11]=[CH:10][CH:9]=2)[C:5]2[C:18]3[C:13]([CH2:12][C:6]1=2)=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:20]=[CH2:19]

Participants

6

Reactant 3

HCID 7841Allyl bromideHCID 14798Sodium HydroxideHCID 131294105,6-Dihydroindeno[2,1-b]indole

Product 1

HCID 17896911HCID 17896911, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 5974Hexadecyltrimethylammonium BromideCatalystHCID 241BenzeneSolvent

Procedure

In a 0.5 l bulb were placed 100 ml 50% aqueous NaOH, 100 ml benzene, 6.1 g (28 mmol)of 5,6-dihydroindeno[2,1-b]indole, prepared in Example 4, 5 g (41 mmol) of allyl-bromide and 0.5 g of trimethylcetylammonium bromide. After having stirred the obtained mixture for 12 hours, the formation of an organic phase was observed; said phase was separated, washed twice with water (100 ml) and dried over Na2SO4. After removal of the solvent, the residue was passed through a column of silicagel, eluted with hexane/ethylacetate=5:1); the resulting solution was evaporated, obtaining 1.8 g of N-allyl-5,6-dihydroindeno[2,1-b]indole (yield=37%).

Workup

  1. customwas separated
  2. washwashed twice with water (100 ml)
  3. dry with materialdried over Na2SO4
  4. customAfter removal of the solvent
  5. washeluted with hexane/ethylacetate=5:1)
  6. customthe resulting solution was evaporated

Sources & evidence

ORD record
ord-ae87bebf6ca440a494c85c3ae9f11f1d
Source dataset
uspto-grants-2002_09
Patent number
US06451724B1

Reaction notes

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