Phenol → HCID 178479472, compound

HRID 1702606

Reaction equation

HRID 1702606 reaction equation
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].[C:16]1(O)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C1(N=C=NC2CCCCC2)CCCCC1>N1C=CC=CC=1>[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4]

Participants

5

Reactant 3

HCID 996PhenolHCID 10868DicyclohexylcarbodiimideHCID 178479474HCID 178479474, compound

Product 1

HCID 178479472HCID 178479472, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (11.8 g), phenol (5.6 g), and dicyclohexylcarbodiimide (12.4 g) in pyridine (75 ml) was stirred overnight at room temperature. After evaporation of solvent, the residue was treated with 0.1 N hydrochloric acid (200 ml), the insoluble materials removed by filtration and the filtrate was washed with ethylacetate. The aqueous layer was concentrated to 100 ml, the resulting crystals were filtered and washed with isopropylalcohol/isopropylether to give phenyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride (12.5 g, 80.2%), m.p. 150°-153° C. This compound was recrystallized from methanol to give white crystal, phenyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride, m.p. 159.5°-161.5° C.

Workup

  1. customAfter evaporation of solvent
  2. additionthe residue was treated with 0.1 N hydrochloric acid (200 ml)
  3. customthe insoluble materials removed by filtration
  4. washthe filtrate was washed with ethylacetate
  5. concentrationThe aqueous layer was concentrated to 100 ml
  6. filtrationthe resulting crystals were filtered
  7. washwashed with isopropylalcohol/isopropylether

Sources & evidence

ORD record
ord-281cb1d74fd14f1ab2f24d483ac632e2
Source dataset
uspto-grants-1982_09
Patent number
US04348410

Linked notes

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