Dicyclohexylcarbodiimide → HCID 20074099, compound

HRID 704413Notes

Reaction equation

HRID 704413 reaction equation
Br.N1C=CC=C(C2CC([C:13](O)=[O:14])CN=2)C=1.[CH2:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[CH:29]1(N=C=NC2CCCCC2)[CH2:34]CCC[CH2:30]1.O[N:45]1[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][C:48]=2[N:47]=N1>CN(C)C=O>[CH2:16]([N:23]1[CH2:24][CH2:25][N:26]([C:13]([CH:49]2[NH:45][C:52]([C:53]3[CH:48]=[N:47][CH:30]=[CH:29][CH:34]=3)=[CH:51][CH2:50]2)=[O:14])[CH2:27][CH2:28]1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 27365101-HeptylpiperazineHCID 67934630HCID 67934630, compound

Product 1

HCID 20074099HCID 20074099, compoundYield 68.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.15 g of 2-(3-pyridyl)-1-pyrroline-4-carboxylic acid monohydrobromide, 770 mg of 1-heptylpiperazine, 860 mg of dicyclohexylcarbodiimide and 560 mg of 1-hydroxybenzotriazole in 15 ml of N,N-dimethylformamide was stirred at room temperature for 3 days. After dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off, the filtrate was concentrated under reduced pressure and, after addition of 0.5N aqueous sodium hydroxide, the residue was extracted with ethyl acetate. The organic layer was extracted with 1N hydrochloric acid. The aqueous layer was adjusted to pH 10 by addition of potassium carbonate and extracted again with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (15 g). Elution with ethyl acetate gave 1.01 g of 1-heptyl-4-[2-(3-pyridyl)-2-pyrrolin-5-ylcarbonyl]piperazine.

Workup

  1. filtrationAfter dilution of the reaction mixture with ethyl acetate, the insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionafter addition of 0.5N aqueous sodium hydroxide
  4. extractionthe residue was extracted with ethyl acetate
  5. extractionThe organic layer was extracted with 1N hydrochloric acid
  6. additionThe aqueous layer was adjusted to pH 10 by addition of potassium carbonate
  7. extractionextracted again with ethyl acetate
  8. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated under reduced pressure
  11. washElution with ethyl acetate

Sources & evidence

ORD record
ord-e95557482fc64ef3bc6219fb5a456482
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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