Dicyclohexylcarbodiimide → HCID 13188155, compound

HRID 1388850Notes

Reaction equation

HRID 1388850 reaction equation
Cl.[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].[C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1O)#[N:17].C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[C:2]([N:5]1[CH2:10][CH2:9][CH:8]([CH2:11][CH2:12][C:13]([O:15][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[C:16]#[N:17])=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 119072-HydroxybenzonitrileHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 13188155HCID 13188155, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4.0 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 2.0 g of o-cyanophenol and 3.5 g of dicyclohexylcarbodiimide was stirred at room temperature for 24 hours in 20 ml of dry pyridine. Any insoluble materials were filtered and washed with dry pyridine. The filtrate and washings were combined together, and the solvent was removed under reduced pressure. Ethyl acetate was added to the residue to give crystals which were then recrystallized from water to obtain 2.1 g (yield: 37%) of o-cyanophenyl 1-amidino-4-piperidinepropionate as colorless crystals having a melting point of 159.5° to 162.5° C.

Workup

  1. filtrationAny insoluble materials were filtered
  2. washwashed with dry pyridine
  3. customthe solvent was removed under reduced pressure
  4. additionEthyl acetate was added to the residue
  5. customto give crystals which
  6. customwere then recrystallized from water

Sources & evidence

ORD record
ord-8fd675713aea49cc9ff383f13f428216
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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