Acetic Acid → HCID 23084217, compound

HRID 1162281Notes

Reaction equation

HRID 1162281 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[C:5]([CH:7]=O)[N:6]=1.[NH2:9][CH:10]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12][CH2:11]1.[C:23](O)(=[O:25])C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:16]([N:13]1[CH2:14][CH2:15][CH:10]([N:9]2[CH2:7][C:5]3=[CH:4][N:3]=[C:2]([CH3:1])[N:6]3[C:23]2=[O:25])[CH2:11][CH2:12]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 4158521-Benzyl-4-piperidylamineHCID 5049666Sodium triacetoxyborohydrideHCID 178418999HCID 178418999, compound

Product 1

HCID 23084217HCID 23084217, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-methylimidazole-4-carbaldehyde (11.0 g), 4-amino-1-benzylpiperidine (19 g) and acetic acid (6.7 ml) in 1,2-dichloroethane (200 ml), under ice-cooling, was added sodium triacetoxyborohydride (32 g), and mixed at room temperature for 15 hours. 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 then the residue was dissolved in THF (200 ml), N,N′-carbonyldiimidazole (18 g) and DBU (17 g) were added thereto, and mixed at room temperature for 15 hours. The reaction solution was concentrated, water was added thereto, and the reaction mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified with silica gel column to obtain the title compound (19 g, 60%).

Workup

  1. additionmixed at room temperature for 15 hours
  2. washThe reaction solution was washed with an aqueous potassium carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. dissolutionthe residue was dissolved in THF (200 ml)
  6. additionN,N′-carbonyldiimidazole (18 g) and DBU (17 g) were added
  7. additionmixed at room temperature for 15 hours
  8. concentrationThe reaction solution was concentrated
  9. additionwater was added
  10. extractionthe reaction mixture was extracted with ethyl acetate
  11. dry with materialThe extract was dried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified with silica gel column

Sources & evidence

ORD record
ord-6a5d1faaaa5f4aba8ad9802d02788c4d
Source dataset
uspto-grants-2010_10
Patent number
US07820673B2

Reaction notes

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