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

HRID 1462890Notes

Reaction equation

HRID 1462890 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-c9504ad916414e168f7d4e1ece24b758
Source dataset
uspto-grants-1984_07
Patent number
US04461894

Reaction notes

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