Sodium Hydroxide → Lifarizine

HRID 847437Notes

Reaction equation

HRID 847437 reaction equation
O[CH2:2][C:3]1[N:4]=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)[NH:6][C:7]=1[CH3:8].[C:16]1([CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:23]2[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[OH-].[Na+].[Br-].[Li+]>C(O)C.O>[C:29]1([CH:22]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:23]2[CH2:24][CH2:25][N:26]([CH2:2][C:3]3[N:4]=[C:5]([C:9]4[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=4)[NH:6][C:7]=3[CH3:8])[CH2:27][CH2:28]2)[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 70048BenzhydrylpiperazineHCID 82050Lithium BromideHCID 22412356[5-Methyl-2-(4-methylphenyl)-1H-imidazol-4-yl]methanol

Product 1

HCID 71336LifarizineYield 88%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

One mole of 4-hydroxymethyl-2-(4-methylpheny)-5-methyl-1H-imidazole (202 g) was dissolved in 2 liters of 95% ethanol, then 252 g (1 mole) of N-(diphenylmethyl)piperazine was added portionwise. This was followed by the addition of 1 liter of water, 60 g (1.5 mole) of sodium hydroxide (as 12N solution) and 8.7 g (0.1 mole) of lithium bromide. The reaction medium was refluxed for 5 hours, allowed to cool to room temperature, and was stirred overnight. The precipitate that formed was filtered and purified by reslurrying from 1.2 liters of an ethanol-water mixture (60/40) to produce the 383.6 g of the title compound (0.88 mole, 88% yield), having a melting point of 238° C.

Workup

  1. temperatureThe reaction medium was refluxed for 5 hours
  2. customThe precipitate that formed
  3. filtrationwas filtered
  4. custompurified

Sources & evidence

ORD record
ord-9c6545fc79a941ea9dfb4e9db6c38caf
Source dataset
uspto-grants-1992_08
Patent number
US05142052

Reaction notes

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