Benzamidine → HCID 70531897, compound

HRID 2287141Notes

Reaction equation

HRID 2287141 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([N:7]=[C:8](Cl)[Cl:9])=[CH:3][CH:2]=1.[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.[C:18]([NH2:26])(=[NH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>CCOCC.O1CCCC1>[ClH:9].[NH2:26][C:18](=[N:25][C:8]([N:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]1)=[N:7][C:4]1[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 2332BenzamidineHCID 12145Phenylimidocarbonyl chlorideHCID 531671-Methylpiperazine

Product 1

HCID 70531897HCID 70531897, compoundYield 32.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

To 3.48 g (0.02 mol) of phenylisocyanide dichloride in 25 ml of anhydrous ether at 0° C. under a nitrogen atmosphere was added 4.0 g (0.04 mol) of 1-methylpiperazine in 20 ml of anhydrous ether dropwise. The mixture was stirred for one hour at ambient temperature and filtered to remove the precipitated 1-methylpiperazine hydrochloride. The filtrate was added dropwise to a solution of 4.8 g (0.04 mol) of benzamidine in 15 ml of tetrahydrofuran. The mixture was stirred for 20 hours at ambient temperature. The precipitated product was collected and reprecipitated twice by pouring a methanolic solution of the product into a large excess of anhydrous ether. The product was subsequently recrystallized from methanol-ether to afford 2.30 g (32%) of N-(1-amino-1-phenylmethylene)-N'-(phenyl)-1-methyl-4-piperazinecarboximidamide hydrochloride, mp 247°-248° C.

Workup

  1. filtrationfiltered
  2. customto remove the precipitated 1-methylpiperazine hydrochloride
  3. stirringThe mixture was stirred for 20 hours at ambient temperature
  4. customThe precipitated product was collected
  5. customreprecipitated twice
  6. additionby pouring a methanolic solution of the product into a large excess of anhydrous ether
  7. customThe product was subsequently recrystallized from methanol-ether

Sources & evidence

ORD record
ord-79b372801741433cbef85924543a9587
Source dataset
uspto-grants-1981_05
Patent number
US04269837

Reaction notes

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