Sodium Bicarbonate → HCID 67297399, compound

HRID 2047641Notes

Reaction equation

HRID 2047641 reaction equation
[C:1]1([C:7]2[N:11]=[C:10]([CH:12]3[CH2:17][CH2:16][NH:15][C:14](=[O:18])[CH2:13]3)[O:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.F[B-](F)(F)F.[CH3:24][O+](C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:24][O:18][C:14]1[CH2:13][CH:12]([C:10]2[O:9][N:8]=[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[N:11]=2)[CH2:17][CH2:16][N:15]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 67300490HCID 67300490, compound

Product 1

HCID 67297399HCID 67297399, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add 4-(3-phenyl-1,2,4-oxadiazol-5-yl)piperidin-2-one (1.0 g, 4.11 mmol) to a solution of trimethyloxonium tetrafluoroborate (1.06 g, 6.99 mmol) in dichloromethane (8.2 mL) at 0° C. Stir the reaction overnight at room temperature and pour into an ice cold solution of saturated aqueous sodium bicarbonate. Separate and extract the aqueous layer with additional dichloromethane. Combine the organic layers, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to afford the title compound as a crystalline white solid (0.96 g). 1H NMR (CDCl3) δ 1.9 (m, 1H), 2.17 (m, 1H), 2.65-2.72 (m, 2H), 3.43 (m, 1H), 3.58 (m, 1H), 3.7 (s, 3H), 3.75 (m, 1H), 7.43-7.53 (m, 3H), 8.0-8.1 (m, 2H).

Workup

  1. customthe reaction overnight at room temperature
  2. customSeparate
  3. extractionextract the aqueous layer with additional dichloromethane
  4. dry with materialdry over anhydrous sodium sulfate
  5. filtrationfilter
  6. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-2ac9168016f5497bb282e124f0365db3
Source dataset
uspto-grants-2013_11
Patent number
US08592590B2

Reaction notes

Loading…