Dicyclohexylcarbodiimide → HCID 86739280, compound

HRID 1388853Notes

Reaction equation

HRID 1388853 reaction equation
[ClH:1].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([OH:15])=[O:14])[CH2:7][CH2:6]1)(=[NH:4])[NH2:3].[NH:16]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1O)[C:17]([CH3:19])=[O:18].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[ClH:1].[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([O:15][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[NH:16][C:17]([CH3:19])=[O:18])=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 119722-AcetamidophenolHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 86739280HCID 86739280, compoundYield 92.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 2.6 g of o-acetaminophenol was dissolved in 40 ml of dry pyridine. To the solution was added with ice-cooling and stirring 3.5 g of dicyclohexylcarbodiimide, and the resulting mixture was allowed to stand at room temperature for 44 hours. After removal of any insoluble materials, the solvent was removed under reduced pressure. The residue was washed with ethyl acetate, and dry ether was then added to the residue to give crystals. The crystals were washed with ether several times, then with warm dichloromethane and finally with ethyl acetate. Dry ether was added to the crystals, and the mixture was evaporated to dryness to obtain 5.8 g (yield: 92.7%) of o-acetaminophenyl 1-amidino-4-piperidinepropionate hydrochloride as hygroscopic crystals.

Workup

  1. additionTo the solution was added with ice-
  2. temperaturecooling
  3. customAfter removal of any insoluble materials
  4. customthe solvent was removed under reduced pressure
  5. washThe residue was washed with ethyl acetate, and dry ether
  6. additionwas then added to the residue
  7. customto give crystals
  8. washThe crystals were washed with ether several times
  9. additionDry ether was added to the crystals
  10. customthe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-f9de15746f1741ed8e413221d3b5eb5b
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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