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

HRID 1612788Notes

Reaction equation

HRID 1612788 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-042c9cd72d534454a307ccc2f9b9a688
Source dataset
uspto-grants-1993_03
Patent number
US05190960

Reaction notes

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