Potassium Hydroxide → 3-[[2-{1-(4-Fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate

HRID 54562Notes

Reaction equation

HRID 54562 reaction equation
Cl.N1CCC(CCNC(C2N=C(C3C=CC(C#N)=CC=3)ON=2)=O)CC1.FC1C=CC(C=O)=CC=1.[OH-].[K+].[BH4-].[Na+].[F:39][C:40]1[CH:70]=[CH:69][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH:48]([CH2:51][CH2:52][NH:53][C:54]([C:56]3[N:60]=[C:59]([C:61]4[CH:66]=[CH:65][C:64]([C:67]#[N:68])=[CH:63][CH:62]=4)[O:58][N:57]=3)=[O:55])[CH2:47][CH2:46]2)=[CH:42][CH:41]=1.[C:71]([OH:78])(=[O:77])/[CH:72]=[CH:73]/[C:74]([OH:76])=[O:75]>CO.C(O)C>[C:71]([OH:78])(=[O:77])/[CH:72]=[CH:73]/[C:74]([OH:76])=[O:75].[F:39][C:40]1[CH:41]=[CH:42][C:43]([CH2:44][N:45]2[CH2:50][CH2:49][CH:48]([CH2:51][CH2:52][NH:53][C:54]([C:56]3[N:60]=[C:59]([C:61]4[CH:62]=[CH:63][C:64]([C:67]#[N:68])=[CH:65][CH:66]=4)[O:58][N:57]=3)=[O:55])[CH2:47][CH2:46]2)=[CH:69][CH:70]=1

Participants

9

Reactant 6

HCID 14797Potassium HydroxideHCID 680234-FluorobenzaldehydeHCID 444972Fumaric AcidHCID 4311764Sodium borohydrideHCID 98457333-[[2-{1-(4-Fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazoleHCID 199592533-[{2-(Piperidin-4-yl)ethyl}carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole hydrochloride

Product 1

HCID 199592613-[[2-{1-(4-Fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent2×

Procedure

To a mixture of 3-[{2-(piperidin-4-yl)ethyl}carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole hydrochloride (0.7 g), 4-fluorobenzaldehyde (0.24 g) and molecular sieves 4A (1.0 g) in methanol (7 ml) was added 1M solution of potassium hydroxide in methanol (1.93 ml). After stirring for 5 hours at ambient temperature, sodium borohydride (73 mg) was added to the mixture under ice cooling. The mixture was stirred for 20 minutes and evaporated in vacuo. The residue was dissolved in ethyl acetate and washed with water, brine, dried over magnesium sulfate and evaporated in vacuo to give a residue containing 3-[[2-{1-(4-fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole. The residue and fumaric acid (0.11 g) were dissolved in hot ethanol (10 ml) and recrystallized to afford 3-[[2-{1-(4-fluorobenzyl)piperidin-4-yl}ethyl]carbamoyl]-5-(4-cyanophenyl)-1,2,4-oxadiazole fumarate (0.50 g).

Workup

  1. stirringThe mixture was stirred for 20 minutes
  2. customevaporated in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a residue
  8. customrecrystallized

Sources & evidence

ORD record
ord-ce154569607b4a6aae09e56b9c7bffc2
Source dataset
uspto-grants-1997_04
Patent number
US05622976

Reaction notes

Loading…