Piperidine → Oxazolo(4,5-b)pyridin-2(3H)-one, 3-(2-(1-piperidinyl)ethyl)-

HRID 465983Notes

Reaction equation

HRID 465983 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[O:6][C:5]1=[O:13].[NH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C>C(#N)C>[N:14]1([CH2:2][CH2:3][N:4]2[C:8]3=[N:9][CH:10]=[CH:11][CH:12]=[C:7]3[O:6][C:5]2=[O:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 81531DiisopropylethylamineHCID 103771063-(2-Bromoethyl)oxazolo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 3072032Oxazolo(4,5-b)pyridin-2(3H)-one, 3-(2-(1-piperidinyl)ethyl)-

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

0.01 mol of 3-(2-bromoethyl)-3H-oxazolo[4,5-b]pyridin-2-one, dissolved in acetonitrile, 0.15 mol of piperidine and 0.015 mol of diisopropylethylamine are introduced into a round-bottomed flask placed under argon and surmounted by a condenser. The mixture is brought to 80° C. for 12 hours. It is cooled, the acetonitrile is evaporated off under vacuum and the residue is taken up with water. The alkalinity of the medium is checked and the medium is extracted with dichloromethane. The organic phase is dried over magnesium sulfate and evaporated and the residue is recrystallized.

Workup

  1. customsurmounted by a condenser
  2. temperatureIt is cooled
  3. customthe acetonitrile is evaporated off under vacuum
  4. extractionthe medium is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. customevaporated
  7. customthe residue is recrystallized

Sources & evidence

ORD record
ord-5888d9e0e8b243429b26f163cae7d0b0
Source dataset
uspto-grants-1992_10
Patent number
US05155116

Reaction notes

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