Triethylamine → N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-(3-phenyl-1H-1,2,4-triazol-5-yl)acetamide

HRID 1070506Notes

Reaction equation

HRID 1070506 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([CH2:12][C:13]([OH:15])=O)[NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:21][N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:17][C:18]1[CH:19]=[C:20]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:21][N:22]1[CH2:23][CH2:24][CH:25]([NH:28][C:13](=[O:15])[CH2:12][C:10]2[NH:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:11]=2)[CH2:26][CH2:27]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 17609309(3-Phenyl-1H-1,2,4-triazol-5-yl)acetic acidHCID 223962061-(3,4-Dichloro-benzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 22396175N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-(3-phenyl-1H-1,2,4-triazol-5-yl)acetamideYield 70.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(3-Phenyl-1H-1,2,4-triazol-5-yl)acetic acid (0.020 g) and N,N′-carbonyl diimidazole (0.016 g) in dichloromethane was stirred under nitrogen for 3 minutes. 1-(3,4-Dichlorobenzyl)-4-piperidinamine hydrochloride (0.031 g) and triethylamine (0.036 g) was then added and allowed to stir for 1 hour under nitrogen. Saturated sodium hydrogen carbonate was added to the reaction with the resulting solution being extracted three times with dichloromethane. The pooled organic phases were washed once with water, once with brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to a white solid. This was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile). Saturated sodium hydrogen carbonate was added to the pooled collected fractions with the resulting solution being extracted three times with dichloromethane. The pooled organic phases were washed once with water, once with brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to leave N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-(3-phenyl-1H-1,2,4-triazol-5-yl)acetamide(0.031 g).

Workup

  1. extractionbeing extracted three times with dichloromethane
  2. washThe pooled organic phases were washed once with water, once with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure to a white solid
  6. customThis was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile)
  7. additionSaturated sodium hydrogen carbonate was added to the
  8. custompooled collected fractions with the resulting solution
  9. extractionbeing extracted three times with dichloromethane
  10. washThe pooled organic phases were washed once with water, once with brine
  11. dry with materialdried over magnesium sulfate
  12. filtrationfiltered
  13. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-8a5c7eb50fd24581ae810e34f692c325
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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