Acetic Acid → HCID 23138268, compound

HRID 1162343Notes

Reaction equation

HRID 1162343 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][NH2:16])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1[NH:19][CH:20]=[C:21]([CH:23]=O)[N:22]=1.[C:25](O)(=[O:27])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][N:16]2[CH2:23][C:21]3=[CH:20][N:19]=[C:18]([CH3:17])[N:22]3[C:25]2=[O:27])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 18670022-(1-Benzylpiperidin-4-yl)ethan-1-amineHCID 5049666Sodium triacetoxyborohydrideHCID 178418999HCID 178418999, compound

Product 1

HCID 23138268HCID 23138268, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of 2-(1-benzyl-4-piperidinyl)ethanamine (5.5 g), 2-methylimidazole-4-carbaldehyde (2.8 g) and acetic acid (1.7 ml) in 1,2-dichloroethane (50 ml) was added sodium triacetoxyborohydride (8.1 g) under ice-cooling. The reaction mixture was returned to room temperature and mixed for 15 hours. 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 (50 ml). To the reaction solution were added N,N′-carbonyldiimidazole (4.5 g) and DBU (4.2 g), and mixed at room temperature for 3 hours. The solvent was distilled off under reduced pressure, and the residue was dissolved in ethyl acetate, 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 (4.0 g, 48%).

Workup

  1. temperaturecooling
  2. customwas returned to room temperature
  3. additionmixed for 15 hours
  4. washThen, the reaction solution was washed with an aqueous potassium carbonate solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. dissolutionthe residue was dissolved in THF (50 ml)
  8. additionTo the reaction solution were added N,N′-carbonyldiimidazole (4.5 g) and DBU (4.2 g)
  9. additionmixed at room temperature for 3 hours
  10. distillationThe solvent was distilled off under reduced pressure
  11. dissolutionthe residue was dissolved in ethyl acetate
  12. washwashed with water
  13. dry with materialdried over anhydrous magnesium sulfate
  14. concentrationconcentrated under reduced pressure
  15. customThe residue was purified with basic silica gel column (ethyl acetate)

Sources & evidence

ORD record
ord-5771bc1418784a8ea4daf63d222f28f5
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

Loading…