O-Cresol → HCID 20470349, compound

HRID 1388851Notes

Reaction equation

HRID 1388851 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].[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1O.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:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:16])=[O:14])[CH2:7][CH2:6]1)(=[NH:3])[NH2:4]

Participants

5

Reactant 3

HCID 335O-CresolHCID 10868DicyclohexylcarbodiimideHCID 155835121-Amidino-4-piperidinepropionic acid hydrochloride

Product 1

HCID 20470349HCID 20470349, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 4 g of 1-amidino-4-piperidinepropionic acid hydrochloride, 1.9 of o-methylphenol, 3.5 g of dicyclohexylcarbodiimide and 20 ml of dry pyridine was stirred overnight at room temperature. Any insoluble materials were filtered and washed with pyridine. The filtrate and washings were combined together, and the solvent was removed under reduced pressure. Ethyl acetate and ether were added to the residue to give crystals. After being air-dried, the crystals were recrystallized from water to obtain 3 g (yield: 54%) of -methylphenyl 1-amidino-4-piperidinepropionate hydrochloride as colorless prisms having a melting point of 184° to 185.5° C. The IR and NMR spectra of the compound were identical with those of the compound obtained in Example 28.

Workup

  1. filtrationAny insoluble materials were filtered
  2. washwashed with pyridine
  3. customthe solvent was removed under reduced pressure
  4. additionEthyl acetate and ether were added to the residue
  5. customto give crystals
  6. customAfter being air-dried
  7. customthe crystals were recrystallized from water

Sources & evidence

ORD record
ord-143aa1a0507d4ec1a3d3c7f5748536b2
Source dataset
uspto-grants-1984_02
Patent number
US04433152

Reaction notes

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