Water → HCID 22285585, compound

HRID 1062443Notes

Reaction equation

HRID 1062443 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.[CH3:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1.[Cl:21][C:22]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=1[C:29]1[N:30]([C:39]2[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=2)[CH:31]=[C:32]([C:34](OCC)=O)[N:33]=1.O>C1COCC1>[Cl:45][C:42]1[CH:41]=[CH:40][C:39]([N:30]2[CH:31]=[C:32]([CH2:34][N:18]3[CH2:19][CH2:20][N:15]([C:12]4[CH:11]=[CH:10][C:9]([CH3:8])=[CH:14][CH:13]=4)[CH2:16][CH2:17]3)[N:33]=[C:29]2[C:23]2[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=2[Cl:21])=[CH:44][CH:43]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11463589HCID 11463589, compoundHCID 21226445Aluminium lithium hydrideHCID 222855141-(4-Methylphenyl)piperazine monohydrochloride

Product 1

HCID 22285585HCID 22285585, compoundYield 2.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (21 mg, 0.54 mmol) in THF (2 mL), 1-(4-methylphenyl)piperazine hydrochloride (32 mg, 0.13 mmol) was added. After 10 minutes, a solution of ethyl 2-(2,4-dichlorophenyl)-1-(4-chlorophenyl)-1H-imidazole-4-carboxylate (39 mg, 0.1 mmol) in THF (2 mL) was added dropwise. The reaction mixture was stirred for 10 minutes, and diluted by water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by HPLC (YMC-packed Pro C18 20×150 mm column, 10-90% CH3CN in H2O/TFA, 25 mL/min) to give the product 1-{[1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-1H-imidazol-4-yl]methyl}-4-(4-methylphenyl)-piperazine (1.4 mg, 2% yield): LC-MS m/z 511.1 (MH+), retention time 2.94 min (method 1). 1H NMR (300 MHz, CDCl3) δ: 2.29 (3H, s), 3.42-3.49 (8H, br), 4.39 (2H, s), 6.85-7.41 (11H, m), 7.54 (1H, s).

Workup

  1. additionwas added
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by HPLC (YMC-packed Pro C18 20×150 mm column, 10-90% CH3CN in H2O/TFA, 25 mL/min)

Sources & evidence

ORD record
ord-8e0e02a126db44309d732372b093505c
Source dataset
uspto-grants-2005_11
Patent number
US06960601B2

Reaction notes

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