Sodium Hydroxide → Lifarizine

HRID 1197456Notes

Reaction equation

HRID 1197456 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([CH3:16])=[C:12]([CH2:14]Cl)[N:13]=2)=[CH:5][CH:4]=1.[C:17]1([CH:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:24]2[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[OH-].[Na+]>C(O)C.O>[C:30]1([CH:23]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:24]2[CH2:25][CH2:26][N:27]([CH2:14][C:12]3[N:13]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([CH3:2])=[CH:4][CH:5]=4)[NH:10][C:11]=3[CH3:16])[CH2:28][CH2:29]2)[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70048BenzhydrylpiperazineHCID 22412164HCID 22412164, compound

Product 1

HCID 71336Lifarizine

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

50 Grams (0.2 mol) of 2-(4-methylphenyl)-4-chloromethyl-5-methyl-1H-imidazole hydrochloride dissolved in 200 ml of a mixture of ethanol:water 6:4 were added dropwise to a refluxing solution of 55 grams (0.2 mol) of N-(diphenylmethyl)piperazine and 24 grams (0.6 mol) sodium hydroxide in 200 ml of a mixture of ethanol:water 6:4. After 2 to 3 hours 1-diphenylmethyl-4-[(2-(4-methylphenyl)-5-methyl-1H-imidazol-4yl)methyl]piperazine precipitated from the reaction mixture. After having left the crystals standing at room temperature, they were removed by filtration and recrystallized from methanol to give the free base which melted at 220°-222° C.

Workup

  1. customAfter 2 to 3 hours 1-diphenylmethyl-4-[(2-(4-methylphenyl)-5-methyl-1H-imidazol-4yl)methyl]piperazine precipitated from the reaction mixture
  2. waitAfter having left the crystals
  3. customstanding at room temperature
  4. customthey were removed by filtration
  5. customrecrystallized from methanol
  6. customto give the free base which melted at 220°-222° C.

Sources & evidence

ORD record
ord-4fc75a90374643de9edf083c81e60653
Source dataset
uspto-grants-1994_01
Patent number
US05276034

Reaction notes

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