Carbazole → HCID 86755445, compound

HRID 1420699Notes

Reaction equation

HRID 1420699 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+].[Na].[Br:17][CH2:18][CH2:19][CH2:20][Cl:21]>CN(C=O)C>[Cl:21][CH2:20][CH2:19][CH2:18][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.[Br:17][CH2:18][CH2:19][CH2:20][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

Participants

6

Reactant 4

HCID 6854CarbazoleHCID 80061-Bromo-3-chloropropaneHCID 24758Sodium hydrideHCID 5360545Sodium

Product 1

HCID 86755445HCID 86755445, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Carbazole (50.0 g, 0.3 mol) was dissolved in dry DMF (1.5 L). NaH (60% in oil, 18.8 g, 0.45 mol) was added under a nitrogen atmosphere. The reaction mixture was stirred at ambient temperature for 3 h. To the resulting sodium salt was carefully added under vigorous stirring a solution of 1-bromo-3-chloropropane in dry DMF (0.5 L). The mixture was stirred at room temperature for 10 h. The solvent was removed in vacuo. The residual oil was dissolved in CH2Cl2 (350 mL), washed with water (3×100 ml), dried (MgSO4), filtered and the solvent removed in vacuo to give a yellow oil. The oil was triturated with cold n-heptane (3×50 mL), and the precipitate collected. This afforded the title compound (48.3 g, 66%) as a yellow solid. M.p. 39-40° C. 1H-NMR (δ CDCl3): 2.3-2.5 (m, 2H); 3.4 (t, 1H); 3.55 (t, 1H); 4.55 (d, t, 2H); 7.35 (m, 2H); 7.5 (d, 2H); 8.1 (d, 2H). The product was isolated as an 1:1 mixture of the 3-bromo- and 3-chloro-derivatives.

Workup

  1. stirringThe mixture was stirred at room temperature for 10 h
  2. customThe solvent was removed in vacuo
  3. dissolutionThe residual oil was dissolved in CH2Cl2 (350 mL)
  4. washwashed with water (3×100 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customto give a yellow oil
  9. customThe oil was triturated with cold n-heptane (3×50 mL)
  10. customthe precipitate collected

Sources & evidence

ORD record
ord-2a1b2e6421fb4d1da46d3a788a7e987a
Source dataset
uspto-grants-2000_06
Patent number
US06071932

Reaction notes

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