Acetic Acid → HCID 23138248, compound

HRID 1162347Notes

Reaction equation

HRID 1162347 reaction equation
Cl.Cl.Cl.[CH2:4]([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][NH2:19])[CH2:13][CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH3:20][C:21]1[NH:22][CH:23]=[C:24]([CH:26]=O)[N:25]=1.[C:28](O)(=[O:30])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:4]([N:11]1[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][N:19]2[CH2:26][C:24]3=[CH:23][N:22]=[C:21]([CH3:20])[N:25]3[C:28]2=[O:30])[CH2:15][CH2:16]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 23138332HCID 23138332, compoundHCID 178418999HCID 178418999, compound

Product 1

HCID 23138248HCID 23138248, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 2-(1-benzyl-4-piperazinyl)ethanamine trihydrochloride (2.5 g) obtained in Example 97a), 2-methylimidazole-4-carbaldehyde (0.84 g) and acetic acid (0.5 ml) in 1,2-dichloroethane (50 ml) was mixed at room temperature for 40 minutes, and then sodium triacetoxyborohydride (2.4 g) was added thereto under ice-cooling. The reaction mixture was returned to room temperature, and mixed for 2 days. Then, the reaction solution was washed with an aqueous potassium carbonate solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was dissolved in THF (60 ml). To the reaction solution were added N,N′-carbonyldiimidazole (1.4 g) and DBU (1.3 g), and mixed at room temperature for 4 days. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, then washed with water, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The residue was purified with basic silica gel column (ethyl acetate) to obtain the title compound as a colorless oil (0.22 g, 8.5%).

Workup

  1. additionwas mixed at room temperature for 40 minutes
  2. temperatureunder ice-cooling
  3. customwas returned to room temperature
  4. additionmixed for 2 days
  5. washThen, the reaction solution was washed with an aqueous potassium carbonate solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. dissolutionthe residue was dissolved in THF (60 ml)
  9. additionTo the reaction solution were added N,N′-carbonyldiimidazole (1.4 g) and DBU (1.3 g)
  10. additionmixed at room temperature for 4 days
  11. distillationThe solvent was distilled off under reduced pressure
  12. dissolutionthe residue was dissolved in ethyl acetate
  13. washwashed with water
  14. dry with materialdried over anhydrous magnesium sulfate
  15. concentrationconcentrated under reduced pressure
  16. customThe residue was purified with basic silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-afce667b313845c382e6a13d37238477
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…