2-Naphthol → HCID 178479471, compound

HRID 1702607

Reaction equation

HRID 1702607 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].[CH:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH:19]=[CH:18][C:17]=1O.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:18]2[CH:17]=[CH:16][C:25]3[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH:19]=2)=[O:14])[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4]

Participants

5

Reactant 3

HCID 86632-NaphtholHCID 10868DicyclohexylcarbodiimideHCID 178479474HCID 178479474, compound

Product 1

HCID 178479471HCID 178479471, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A suspension of trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (47.1 g), β-naphthol (28.8 g) and dicyclohexylcarbodiimide (45.4 g) in pyridine (400 ml) was stirred at room temperature for 24 hours. After evaporation of solvent, to the residue was added water (500 ml), and the mixture was acidified with hydrochloric acid. The resulting white crystals were dissolved in methanol (500 ml). After evaporation of methanol, the residue was recrystallized from methanol to give β-naphtyl trans-4-guanidinomethylcyclohexanecarboxylate hydrochloride (49.1 g, 67.8%), m.p. 195°-202° C.

Workup

  1. customAfter evaporation of solvent
  2. additionto the residue was added water (500 ml)
  3. dissolutionThe resulting white crystals were dissolved in methanol (500 ml)
  4. customAfter evaporation of methanol
  5. customthe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-f9738bda71e149f6b074ac9ff2555b49
Source dataset
uspto-grants-1982_09
Patent number
US04348410

Linked notes

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