Benzamidine, hydrochloride → Dimethyl-[3-(5-phenyl-1H-[1,2,4]triazol-3-yl)-benzyl]-amine hydrochloride

HRID 1386921Notes

Reaction equation

HRID 1386921 reaction equation
[ClH:1].[C:2](N)(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CC[O-].[Na+].[CH3:15][N:16]([CH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][CH:28]=1)[C:22]([NH:24][NH2:25])=O)[CH3:17].Cl.CCOCC>C(O)C>[ClH:1].[CH3:15][N:16]([CH3:17])[CH2:18][C:19]1[CH:28]=[CH:27][CH:26]=[C:21]([C:22]2[N:9]=[C:2]([C:3]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[NH:25][N:24]=2)[CH:20]=1

Participants

6

Reactant 4

HCID 80289Benzamidine, hydrochlorideHCID 2723922Sodium ethoxideHCID 10953452Ether hydrochlorideHCID 635713743-Dimethylaminomethyl-benzoic acid hydrazide

Product 1

HCID 21180508Dimethyl-[3-(5-phenyl-1H-[1,2,4]triazol-3-yl)-benzyl]-amine hydrochlorideYield 27%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred ethanolic suspension of benzamidine hydrochloride salt (235 mg, 1.5 mmol, 1.5 eq.), was added 1.2N NaOEt in ethanol (1.7 ml, 2 eq.) over 3 minutes, the mixture was further stirred for 30 min. at r.t. To this was added 3-dimethylaminomethyl-benzoic acid hydrazide (193 mg, 1 mmol) in ethanol at 20° C. and the mixture heated to reflux for 24 hrs. Upon cooling the product mixture was filtered, solvent evaporated and residue subjected to preparative reversed-phase HPLC purification using a YMC ODS-AQ column (20×50 mm) and a (0.1% trifluoroacetic acid) water-acetonitrile gradient (25 ml/min. flow rate). The pure fractions were concentrated and the product obtained was converted to the hydrochloride salt by addition of excess 2N HCl/ether solution (1.0 ml) followed by solvent evaporation and high vacuum drying to afford the title compound (84 mg, 0.27 mmol, 27% yield) as a yellow foam. MS: m/e=279.4 (M+H+).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 24 hrs
  3. temperatureUpon cooling the product mixture
  4. filtrationwas filtered
  5. customsolvent evaporated
  6. customreversed-phase HPLC purification
  7. concentrationThe pure fractions were concentrated
  8. customthe product obtained
  9. customfollowed by solvent evaporation and high vacuum
  10. customdrying

Sources & evidence

ORD record
ord-ed2a8d9def8745d19a7756e7bf6477d5
Source dataset
uspto-grants-2001_07
Patent number
US06265426B1

Reaction notes

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