Sodium Hydroxide → HCID 22411949, compound

HRID 1197459Notes

Reaction equation

HRID 1197459 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Na+].[ClH:22].[C:23]1([C:29]2[NH:30][C:31]([CH3:37])=[C:32]([CH:34]([Cl:36])[CH3:35])[N:33]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(O)C.O>[ClH:36].[ClH:22].[ClH:36].[C:14]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]2[CH2:9][CH2:10][N:11]([CH:34]([C:32]3[N:33]=[C:29]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[NH:30][C:31]=3[CH3:37])[CH3:35])[CH2:12][CH2:13]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70048BenzhydrylpiperazineHCID 22411958HCID 22411958, compound

Product 1

HCID 22411949HCID 22411949, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

14 Grams (0.052 mol) of N-(diphenylmethyl)piperazine and 6 grams (0.15 mol) of sodium hydroxide were dissolved in 180 ml of a mixture of ethanol:water 60:40. The mixture was heated to reflux, then 2-phenyl-4-(1-chloroethyl)-5-methylimidazole hydrochloride in 180 milliliters of ethanol:water 60:40 were added dropwise. After 4 to 5 hours under reflux, the reaction mixture was allowed to cool to room temperature. The oil that separated was washed twice with water, then dissolved in ether and hydrochloric acid was added. The precipitate was recrystallized from ethanol to give 1-diphenylmethyl-4-[1-(2-phenyl-5-methyl-1H-imidazol-4-yl)ethyl]piperazine trihydrochloride (55% yield), which melted at 215° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. temperatureAfter 4 to 5 hours under reflux
  4. customThe oil that separated
  5. washwas washed twice with water
  6. dissolutiondissolved in ether
  7. additionhydrochloric acid was added
  8. customThe precipitate was recrystallized from ethanol

Sources & evidence

ORD record
ord-477db731022a4824b7a19229065c09c6
Source dataset
uspto-grants-1994_01
Patent number
US05276034

Reaction notes

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