Benzhydrylpiperazine → HCID 18949419, compound

HRID 1768753Notes

Reaction equation

HRID 1768753 reaction equation
[CH2:1]([N:5]1[C:9]([CH:10]=O)=[C:8]([CH3:12])[N:7]=[C:6]1[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[CH:2]([CH3:4])[CH3:3].[C:23]1([CH:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:30]2[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C([BH3-])#N.[Na+]>CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4].C(O)C>[C:36]1([CH:29]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:30]2[CH2:31][CH2:32][N:33]([CH2:10][C:9]3[N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[C:6]([C:13]4[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=4)=[N:7][C:8]=3[CH3:12])[CH2:34][CH2:35]2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 70048BenzhydrylpiperazineHCID 5003444Sodium cyanoborohydrideHCID 18949420HCID 18949420, compound

Product 1

HCID 18949419HCID 18949419, compoundYield 35.5%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolvent

Procedure

A solution of 1-isobutyl-2-(4-trifluoromethylphenyl)-4-methyl-5-formylimidazole (1.6 g), N-(diphenylmethyl)piperazine (1.3 g), and titanium tetraisopropoxide (2 ml) were stirred for 1 hour at room temperature. Ethanol (10 ml) was added, and the resultant solution was stirred for a further 30 minutes. Sodium cyanoborohydride (330 mg) was then added, and the mixture stirred overnight. The solvent was removed under reduced pressure, and the residue partitioned between methylene chloride/water. The organic phase was separated, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was flash-chromatographed on silica gel, eluting with ethyl acetate/n-heptane (1/2), to yield 1.0 g of 1-diphenylmethyl-4-[(1-isobutyl-2-(4-trifluoromethylphenyl)-4-methylimidazol-5-yl)methyl]piperazine. Treatment with anhydrous hydrochloric acid in ethanol converted the base to its trihydrochloride salt, m.p. 200° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue partitioned between methylene chloride/water
  3. customThe organic phase was separated
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was flash-chromatographed on silica gel
  8. washeluting with ethyl acetate/n-heptane (1/2)

Sources & evidence

ORD record
ord-d31c23af677947f9b6af9b63a7d8721d
Source dataset
uspto-grants-1995_01
Patent number
US05378847

Reaction notes

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