Dicyclohexylcarbodiimide → HCID 14881730, compound

HRID 704438Notes

Reaction equation

HRID 704438 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[N:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH:22]2[NH:26][CH:25]([C:27]([OH:29])=O)[CH2:24][S:23]2)[CH:17]=1.[CH2:30]([N:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37].ON1C2C=CC=CC=2N=N1.[C:54]([OH:61])(=[O:60])/[CH:55]=[CH:56]/[C:57]([OH:59])=[O:58]>C(OCC)(=O)C.C(O)C.CN(C)C=O>[C:54]([OH:61])(=[O:60])/[CH:55]=[CH:56]/[C:57]([OH:59])=[O:58].[CH2:30]([N:38]1[CH2:39][CH2:40][N:41]([C:27]([CH:25]2[CH2:24][S:23][CH:22]([C:18]3[CH:17]=[N:16][CH:21]=[CH:20][CH:19]=3)[NH:26]2)=[O:29])[CH2:42][CH2:43]1)[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 3275932-(3-Piridyl)thiazolidine-4-carboxylic acidHCID 444972Fumaric AcidHCID 27370991-Octylpiperazine

Product 1

HCID 14881730HCID 14881730, compoundYield 51.5%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dicyclohexylcarbodiimide (0.82 g) was added to a mixture of 0.84 g of 2-(3-pyridyl)thiazolidine-4-carboxylic acid, 0.79 g of 1-octylpiperazine, 0.54 g of 1-hydroxybenzotriazole and 20 ml of N,N-dimethylformamide with ice cooling, and the resultant mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate, and the insoluble matter was filtered off. The filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The solvent was then distilled off under reduced pressure. Ethyl acetate was added to the residue, the insoluble matter was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent 10% methanol-ethyl acetate), the oil obtained was dissolved in 25 ml of ethanol, and 0.32 g of fumaric acid was added. After allowing the mixture to stand for 2 days, the resultant crystals were collected by filtration, washed with cold ethanol and dried. Thus was obtained 0.72 g of 1-octyl-4-[2-(3-pyridyl)thiazolidin-4-ylcarbonyl]piperazine fumarate. Melting point 135° C.

Workup

  1. filtrationthe insoluble matter was filtered off
  2. washThe filtrate was washed in sequence with saturated aqueous solution of sodium hydrogen carbonate, water and saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was then distilled off under reduced pressure
  5. additionEthyl acetate was added to the residue
  6. filtrationthe insoluble matter was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent 10% methanol-ethyl acetate)
  9. customthe oil obtained
  10. filtrationthe resultant crystals were collected by filtration
  11. washwashed with cold ethanol
  12. customdried

Sources & evidence

ORD record
ord-0d0c6c0a296d4885a6561b9b90efcaee
Source dataset
uspto-grants-1991_01
Patent number
US04987132

Reaction notes

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