Sodium Bicarbonate → HCID 67419126, compound

HRID 919288Notes

Reaction equation

HRID 919288 reaction equation
C([O-])(=O)C.C[O:6][C:7]1[CH:8]=[C:9]([NH+:13]2[CH2:18][C@H:17]([CH3:19])[NH:16][CH2:15][C@H:14]2[CH3:20])[CH:10]=[CH:11][CH:12]=1.C([O-])(O)=O.[Na+]>CO>[CH3:20][C@@H:14]1[CH2:15][NH:16][C@@H:17]([CH3:19])[CH2:18][N:13]1[C:9]1[CH:8]=[C:7]([OH:6])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 117923001HCID 117923001, compound

Product 1

HCID 67419126HCID 67419126, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a round-bottom flask, 715 mg (2.74 mmol) of 12 was dissolved in 10 mL CH3COOH and 5 mL of H2O. To this mixture was added 50 mg of 10% Pd on carbon, and the suspension was heated and stirred at reflux for 12 h. The mixture was cooled, filtered, and the solvents evaporated under reduced pressure. To the residue was added 20 mL of conc. NaHCO3, and this mixture was extracted thoroughly with EtOAc. The pooled organic extracts were washed once with brine, dried over MgSO4, and the solvents removed under reduced pressure to yield 605 mg of an orange oil that was pure (2R,5S)-1-(3-methoxyphenyl)-2,5-dimethylpiperazinium acetate by NMR. 1H NMR (CDCl3) δ 7.21 (t, 1H), 6.73 (dd, 1H), 6.62 (m, 1H), 6.67 (m, 1H), 6.63 (m, 1H), 3.79 (s, 3H), 3.12-2.90 (m, 4H), 2.70 (dd, 1H), 2.46 (dd, 1H), 1.07 (d, 3H), 0.93 (d, 3H). ESIMS: m/z 221 (M+H+, 100). General procedure c. was employed using 363 mg (1.65 mmol) of this oil affording a residue that was dissolved in 5 mL of MeOH and stirred over excess NaHCO3. The mixture was filtered, and the solvents subjected to rotary evaporation to afford a residue that was purified by chromatography affording 215 mg of 13 as a white solid (63% yield). Spectral information for this compound was found to be identical to 17.

Workup

  1. customaffording a residue that
  2. filtrationThe mixture was filtered
  3. customthe solvents subjected to rotary evaporation
  4. customto afford a residue that
  5. customwas purified by chromatography

Sources & evidence

ORD record
ord-942043357a3e4927ba54f75a88e7d763
Source dataset
uspto-grants-2016_03
Patent number
US09273027B2

Reaction notes

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