Potassium Carbonate → HCID 21087562, compound

HRID 659641Notes

Reaction equation

HRID 659641 reaction equation
[CH:1]1[C:13]2[N:12]([CH2:14][CH2:15][CH2:16][N:17]([CH3:19])[CH3:18])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].Cl[CH:25](Cl)[O:26]C.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CO.O>[CH3:19][N:17]([CH3:18])[CH2:16][CH2:15][CH2:14][N:12]1[C:11]2[CH:10]=[CH:9][C:8]([CH:25]=[O:26])=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 21004Methane, dichloromethoxy-HCID 30316Carbazole, 9-(3-(dimethylamino)propyl)-HCID 6451240Aluminum(III) Chloride

Product 1

HCID 21087562HCID 21087562, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A 100-mL round-bottomed flask was charged with a solution of 3-(9H-carbazol-9-yl)-N,N-dimethylpropan-1-amine (500 mg, 1.98 mmol, 1.00 equiv) in DCM (10 mL), aluminum (III) chloride (550 mg, 4.17 mmol, 2.00 equiv), dichloro(methoxy)methane (0.24 mL, 1.10 equiv), water (10 mL) and K2CO3 (20 mL). The resulting mixture was stirred at 0° C. for 20 hours. The reaction progress was monitored by TLC (DCM: MeOH=10:1). Upon completion, the resulting solution was extracted with ethyl acetate (3×30 mL). Combined organic layers were dried over anhydrous sodium sulfate and concentrated on a rotary evaporator affording 9-(3-(dimethylamino)propyl)-9H-carbazole-3-carbaldehyde as yellow oil (0.45 g, 81%).

Workup

  1. extractionUpon completion, the resulting solution was extracted with ethyl acetate (3×30 mL)
  2. dry with materialCombined organic layers were dried over anhydrous sodium sulfate
  3. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-a2e075ffd212454cac68fac13649508c
Source dataset
uspto-grants-2011_12
Patent number
US08080566B1

Reaction notes

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