Hydrochloric Acid → HCID 63136031, compound

HRID 2370028Notes

Reaction equation

HRID 2370028 reaction equation
[CH3:1][C:2]1([C:17]([O:19]CC)=[O:18])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)[CH2:3]1.[Li+].[OH-].Cl>C1COCC1.CO>[CH3:1][C:2]1([C:17]([OH:19])=[O:18])[CH2:7][CH2:6][CH2:5][N:4]([C:8]2[CH:9]=[CH:10][C:11]([N+:14]([O-:16])=[O:15])=[CH:12][CH:13]=2)[CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71226132HCID 71226132, compound

Product 1

HCID 63136031HCID 63136031, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-methyl-1-(4-nitrophenyl)piperidine-3-carboxylate (2.920 g, 9.99 mmol) in THF (12.50 mL) and MeOH (12.5 mL) was added 2 M aqueous solution of LiOH (25 mL, 50 mmol). The resulting yellow solution was stirred at rt for 22 hrs. The reaction was adjusted to pH=5 with 3N aqueous HCl. The solution was extracted with EtOAc (3×). The combined EtOAc extracts were washed with saturated aqueous NaCl (2×), dried over Na2SO4, filtered and concentrated. The obtained yellow solid was dried under high vacuum to give the desired product, 3-methyl-1-(4-nitrophenyl)piperidine-3-carboxylic acid (2.650 g, 9.53 mmol, 95% yield) as a yellow solid. Anal. Calcd. for C13H16N2O4 m/z 264.2, found: 265.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 8.08 (d, J=9.34 Hz, 2H), 6.89 (d, J=9.34 Hz, 2H), 4.13 (d, J=12.64 Hz, 1H), 3.64 (ddd, J=12.50, 4.53, 4.40 Hz, 1H), 3.10-2.99 (m, 1H), 2.94 (d, J=13.19 Hz, 1H), 2.33-2.18 (m, 1H), 1.88-1.69 (m, 2H), 1.53-1.37 (m, 1H), 1.25 (s, 3H).

Workup

  1. extractionThe solution was extracted with EtOAc (3×)
  2. washThe combined EtOAc extracts were washed with saturated aqueous NaCl (2×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe obtained yellow solid was dried under high vacuum

Sources & evidence

ORD record
ord-db7dec258d6944d0824eede16bd29174
Source dataset
uspto-grants-2014_04
Patent number
US08710049B2

Reaction notes

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