Carbazole → N-Benzylcarbazole

HRID 1914259Notes

Reaction equation

HRID 1914259 reaction equation
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1.C1CCCCC1.ClCCl>[CH2:16]([N:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 3

HCID 6854CarbazoleHCID 7498Benzyl BromideHCID 24758Sodium hydride

Product 1

HCID 146485N-Benzylcarbazole

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21916607Dichloromethane cyclohexaneSolvent

Procedure

To a mixture of carbazole (0.87 g, 5 mmoles) in tetrahydrofuran (THF), NaH (0.24 g, 10 mmoles) was slowly added. The mixture was stirred for 1 hour, obtaining a solution. Benzyl bromide (0.89 ml, 7.5 mmoles) was then added dropwise, and the reaction mixture was stirred for 5 hours at room temperature. The reaction was quenched with ice water and THF was evaporated under reduced pressure. The mixture was extracted with ethyl ether (3×5 mL) and the organic phases were collected and combined, dried over MgSO4 and evaporated under reduced pressure. The solid obtained was triturated with n-hexane (10 mL), filtered and used without further purification. The compound obtained is a white solid with melting point of 123° C. and Rf=0.44 in cyclohexane/dichloromethane 4/1.

Workup

  1. additionwas slowly added
  2. customobtaining a solution
  3. stirringthe reaction mixture was stirred for 5 hours at room temperature
  4. customThe reaction was quenched with ice water and THF
  5. customwas evaporated under reduced pressure
  6. extractionThe mixture was extracted with ethyl ether (3×5 mL)
  7. customthe organic phases were collected
  8. dry with materialdried over MgSO4
  9. customevaporated under reduced pressure
  10. customThe solid obtained
  11. customwas triturated with n-hexane (10 mL)
  12. filtrationfiltered
  13. customused without further purification
  14. customThe compound obtained

Sources & evidence

ORD record
ord-cd92a52b54c74e72aa9c54b7e13635be
Source dataset
uspto-grants-2013_12
Patent number
US08610111B2

Reaction notes

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