Sodium Bicarbonate → HCID 68289109, compound

HRID 541416Notes

Reaction equation

HRID 541416 reaction equation
[O:1]=[C:2]1[CH2:7][CH:6]([C:8]2[CH:15]=[CH:14][C:11]([C:12]#[N:13])=[CH:10][CH:9]=2)[CH2:5][CH2:4][NH:3]1.F[B-](F)(F)F.[CH3:21][O+](C)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:21][O:1][C:2]1[CH2:7][CH:6]([C:8]2[CH:9]=[CH:10][C:11]([C:12]#[N:13])=[CH:14][CH:15]=2)[CH2:5][CH2:4][N:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 682889654-(2-Oxo-4-piperidinyl)benzonitrile

Product 1

HCID 68289109HCID 68289109, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a round-bottom flask, was placed a solution of 4-(2-oxopiperidin-4-yl)benzonitrile (347.2, 220 mg, 1.10 mmol, 1.00 equiv) in dichloromethane (10 mL). Trimethyloxonium tetrafluoroborate (244.2 mg, 1.65 mmol, 1.50 equiv) was slowly added and the resulting mixture was stirred for 2 h at room temperature. The pH was carefully adjusted to 8 with sodium bicarbonate (aq.). The organic layer was washed with 2×20 mL of H2O, dried over anhydrous sodium sulfate and concentrated under reduced pressure to yield 212 mg (90%) of the title compound as a white solid.

Workup

  1. customInto a round-bottom flask, was placed
  2. washThe organic layer was washed with 2×20 mL of H2O
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-73e5097cf2874d08a73d8f13ff343b98
Source dataset
uspto-grants-2014_10
Patent number
US08871790B2

Reaction notes

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