Aluminium lithium hydride → 1-(2,3,4-Trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)prop-1-yl]piperazine

HRID 22262Notes

Reaction equation

HRID 22262 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=1[CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][C:28]([C:30]2[N:31]=[C:32]([C:37]3[CH:42]=[CH:41][C:40]([C:43]([F:46])([F:45])[F:44])=[CH:39][CH:38]=3)[N:33]([CH3:36])[C:34]=2[CH3:35])=O)[CH2:22][CH2:21]1>O1CCCC1>[CH3:7][O:8][C:9]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[CH:11][C:10]=1[CH2:19][N:20]1[CH2:25][CH2:24][N:23]([CH2:26][CH2:27][CH2:28][C:30]2[N:31]=[C:32]([C:37]3[CH:38]=[CH:39][C:40]([C:43]([F:45])([F:44])[F:46])=[CH:41][CH:42]=3)[N:33]([CH3:36])[C:34]=2[CH3:35])[CH2:22][CH2:21]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57152953HCID 57152953, compound

Product 1

HCID 158190381-(2,3,4-Trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)prop-1-yl]piperazineYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of lithium aluminum hydride (0.6 g) and 1-(2,3,4-trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)-3-oxoprop-1-yl]piperazine (2 g) in 50 ml of tetrahydrofuran was refluxed for 48 hours Excess reagent was hydrolysed by cooling the mixture to 0° C. and adding wet tetrahydrofuran dropwise. The mixture was filtered, the solid washed with a mixture of 1:1 ethanol/isopropanol, solvent evaporated from the filtrate, and the residue flash-chromatographed on silica gel, eluting with 2% methanol in dichloromethane, to yield 400 mg of 1-(2,3,4-trimethoxyphenyl)methyl-4-[(2-(4-trifluoromethylphenyl)-1,5-dimethylimidazol-4-yl)prop-1-yl]piperazine, which was converted to its hydrochloride salt, m.p. 212° C.

Workup

  1. filtrationThe mixture was filtered
  2. washthe solid washed with a mixture of 1:1 ethanol/isopropanol, solvent
  3. customevaporated from the filtrate
  4. customthe residue flash-chromatographed on silica gel
  5. washeluting with 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-9d87755afb75422285b86f37e7eb57a2
Source dataset
uspto-grants-1995_06
Patent number
US05428037

Reaction notes

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