Potassium Carbonate → HCID 54534921, compound

HRID 1953027Notes

Reaction equation

HRID 1953027 reaction equation
C(=O)([O-])[O-].[K+].[K+].[NH:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:8]1.[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32]Cl)[CH3:28]>CN(C)C=O>[CH2:27]([N:29]([CH2:34][CH3:35])[CH2:30][CH2:31][CH2:32][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH2:16][C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[CH:8]1)[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 669183-Chloropropyl(diethyl)amine2×HCID 19603827Benzyl (1H-indol-3-yl)acetate

Product 1

HCID 54534921HCID 54534921, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

At a temperature of about +50° C., 6.2 g (44.9 mMol) of potassium carbonate were added to a solution of 4.0 g (15.1 mMol) of phenylmethyl 1H-indole-3-acetate in 40 ml of dimethylformamide and then at the same temperature a solution of 3.0 g (20.0 mMol) of 3-(diethylamino)propylchloride in 5 ml of dimethylformamid were added dropwise. The mixture was stirred for a further hour at 50° C. and overnight at ambient temperature, heated up to 100° C. again and once more 1.0 g of 3-(diethylamino)propylchloride were added. After stirring for 5 hours at ambient temperature, the mixture was stirred into 300 ml of ice water and extracted exhaustively with diisopropylether. The combined organic extracts were washed with saturated saline solution, dried over magnesium sulphate, clarified with activated charcoal and evaporated down under reduced pressure. A colourless oil was obtained in a yield of 5.37 g (94% of theory) and was used in the following step without further purification.

Workup

  1. temperatureheated up to 100° C. again
  2. stirringAfter stirring for 5 hours at ambient temperature
  3. extractionextracted exhaustively with diisopropylether
  4. washThe combined organic extracts were washed with saturated saline solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated down under reduced pressure
  7. customA colourless oil was obtained in a yield of 5.37 g (94% of theory)
  8. customwas used in the following step without further purification

Sources & evidence

ORD record
ord-d455d877cf614c7dbadaeb976f4a1530
Source dataset
uspto-grants-2000_09
Patent number
US06114390

Reaction notes

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