Sodium Hydroxide → 2-{1-[4-(dipropylamino)butyl]-4-piperidinyl}-N,N-bis(1H-imidazol-2-ylmethyl)acetamide

HRID 68651Notes

Reaction equation

HRID 68651 reaction equation
Cl.Cl.Cl.[NH:4]1[CH:8]=[CH:7][N:6]=[C:5]1[CH2:9][N:10]([CH2:20][C:21]1[NH:22][CH:23]=[CH:24][N:25]=1)[C:11](=[O:19])[CH2:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.[CH2:26]([N:29]([CH2:35][CH2:36][CH3:37])[CH2:30][CH2:31][CH2:32][CH:33]=O)[CH2:27][CH3:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C>[CH2:35]([N:29]([CH2:26][CH2:27][CH3:28])[CH2:30][CH2:31][CH2:32][CH2:33][N:16]1[CH2:17][CH2:18][CH:13]([CH2:12][C:11]([N:10]([CH2:20][C:21]2[NH:22][CH:23]=[CH:24][N:25]=2)[CH2:9][C:5]2[NH:4][CH:8]=[CH:7][N:6]=2)=[O:19])[CH2:14][CH2:15]1)[CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 226111444-(Dipropylamino)butanalHCID 67163702N,N-bis(1H-imidazol-2-ylmethyl)-2-(4-piperidinyl)acetamide trihydrochloride

Product 1

HCID 583003902-{1-[4-(dipropylamino)butyl]-4-piperidinyl}-N,N-bis(1H-imidazol-2-ylmethyl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The compound 45 and 4-(dipropylamino)butanal (55.6 mg) were added and a 10% acetic acid-anhydrous dimethyl formamide solution (3 mL) was stirred under an argon atmosphere for 5 minutes. To the reaction solution, sodium triacetoxyborohydride (103 mg) was added, followed by stirring at room temperature for 15 hours. To the reaction solution, an aqueous 2N sodium hydroxide solution (10 mL) was added and the aqueous layer was extracted three times with ethyl acetate. The organic layer was collected, washed with saturated brine, dried over anhydrous sodium sulfate, and then the solvent was distilled off. The residue was purified by silica gel column chromatography to obtain the title compound (86.4 mg) having the following physical properties.

Workup

  1. extractionthe aqueous layer was extracted three times with ethyl acetate
  2. customThe organic layer was collected
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2f2489421e5740369ee5e11b4fb07974
Source dataset
uspto-grants-2014_09
Patent number
US08822459B2

Reaction notes

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