Triethylamine → 1H-Naphth(1,2-d)imidazole, 2-(2-(4-(4-chlorophenyl)-1-piperazinyl)ethyl)-1-methyl-

HRID 2198988Notes

Reaction equation

HRID 2198988 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C(N(CC)CC)C.Cl[CH2:24][CH2:25][C:26]1[N:30]([CH3:31])[C:29]2[C:32]3[C:37]([CH:38]=[CH:39][C:28]=2[N:27]=1)=[CH:36][CH:35]=[CH:34][CH:33]=3>C(O)C>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([N:10]2[CH2:15][CH2:14][N:13]([CH2:24][CH2:25][C:26]3[N:30]([CH3:31])[C:29]4[C:32]5[C:37]([CH:38]=[CH:39][C:28]=4[N:27]=3)=[CH:36][CH:35]=[CH:34][CH:33]=5)[CH2:12][CH2:11]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12212341Piperazine, 1-(4-chlorophenyl)-, hydrochloride (1:2)HCID 13806193HCID 13806193, compound

Product 1

HCID 30622191H-Naphth(1,2-d)imidazole, 2-(2-(4-(4-chlorophenyl)-1-piperazinyl)ethyl)-1-methyl-Yield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

6.5 g (0.024 mole) of 1-(4-chlorophenyl)-piperazine dihydrochloride and 8.43 cc (0.06 mole) of triethylamine are added to a solution of 2.93 g (0.012 mole) of 2-(2-chloroethyl-1-methyl-1H-naphth[1,2-d]imidazole in 100 cc of ethanol. The reaction mixture is then heated at reflux temperature and maintained under an argon atmosphere for 23 hours. By evaporating the solvent, grinding the residue with water and filtering, a raw product is obtained, which is recrystallized from methylisopropylketone, yielding 4.36 g (90% yield) of pure compound. M.p. 213°-15° C.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureat reflux temperature
  3. temperaturemaintained under an argon atmosphere for 23 hours
  4. customBy evaporating the solvent
  5. customgrinding the residue with water
  6. filtrationfiltering
  7. customa raw product is obtained
  8. customwhich is recrystallized from methylisopropylketone

Sources & evidence

ORD record
ord-12f056b2a8954a36a75c0a4ccc3f16b6
Source dataset
uspto-grants-1982_11
Patent number
US04360674

Reaction notes

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