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

HRID 1070507Notes

Reaction equation

HRID 1070507 reaction equation
[C:1]1([C:7]2[O:11][C:10]([CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[Cl:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:22][N:23]1[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]1.C(N(CC)CC)C.[C:41](=[O:44])([O-])O.[Na+]>ClCCl>[C:14]([OH:16])(=[O:15])[CH3:13].[Cl:18][C:19]1[CH:20]=[C:21]([CH:30]=[CH:31][C:32]=1[Cl:33])[CH2:22][N:23]1[CH2:24][CH2:25][CH:26]([NH:29][C:41](=[O:44])[CH2:12][C:10]2[O:11][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[N:8][N:9]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 71306335-Phenyl-1,3,4-oxadiazole-2-propionic acidHCID 223962061-(3,4-Dichloro-benzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 68884472N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-(5-phenyl-1,3,4-oxadiazol-2-yl)acetamide acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(5-Phenyl-1,3,4-oxadiazol-2-yl)propanoic acid (0.175 g) and N,N′-carbonyldiimidazole (0.148 g) in dichloromethane was stirred under nitrogen for 30 minutes. 1-(3,4-Dichlorobenzyl)-4-piperidinamine hydrochloride (0.263 g), and triethylamine (0.126 g) was then added and allowed to stir for 2 hours 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 leave a cream solid. This solid was purified by chromatography using 2.5% ethanol/dichloromethane. The solvent was removed under reduced pressure and was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile) followed by 1 ml of glacial acetic acid being added and the solvent removed under reduced pressure to leave N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-(5-phenyl-1,3,4-oxadiazol-2-yl)acetamide acetate (0.024 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
  6. customto leave a cream solid
  7. customThis solid was purified by chromatography
  8. customThe solvent was removed under reduced pressure
  9. customwas purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile)
  10. additionadded
  11. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-bf72c310318e44989af2f24c9c32c9fd
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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