Dichloromethane → Carbazole, 9-(3-(dimethylamino)propyl)-

HRID 659640Notes

Reaction equation

HRID 659640 reaction equation
[H-].[Na+].Cl.[CH3:4][NH:5][CH3:6].Br[CH2:8][CH2:9][CH2:10][N:11]1[C:23]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[CH:15][CH:16]=2.C(Cl)Cl>CN(C=O)C.CO>[CH:22]1[C:23]2[N:11]([CH2:10][CH2:9][CH2:8][N:5]([CH3:6])[CH3:4])[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10473Dimethylamine, hydrochlorideHCID 24758Sodium hydrideHCID 10732069N-(3-Bromopropyl)carbazole

Product 1

HCID 30316Carbazole, 9-(3-(dimethylamino)propyl)-Yield 84.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

A 250-mL round-bottomed flask was charged with NaH (5.6 g, 140.00 mmol, 4.00 equiv, 60%) in DMF (100 mL). To this was added dimethylamine hydrochloride (4.23 g, 52.22 mmol, 1.50 equiv) in DMF (50 mL) at room temperature. To this mixture 9-(3-bromopropyl)-9H-carbazole (10 g, 34.70 mmol, 1.00 equiv) was added and the resulting mixture was stirred at room temperature for 4 hours. The reaction progress was monitored by TLC (DCM:MeOH=10:1). Upon completion, the reaction was then quenched by the addition of ice/salt (100 mL). The resulting mixture was extracted with ethyl acetate (3×50 mL). Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator affording 3-(9H-carbazol-9-yl)-N,N-dimethylpropan-1-amine as yellow oil (7.37 g, 80%).

Workup

  1. customUpon completion, the reaction was then quenched by the addition of ice/salt (100 mL)
  2. extractionThe resulting mixture was extracted with ethyl acetate (3×50 mL)
  3. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-74d91b249cd54b32b0f2a06093a10b46
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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