Hydrochloric Acid → HCID 45496772, compound

HRID 2206247Notes

Reaction equation

HRID 2206247 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]2)=[CH:6][CH:5]=1)([O-])=O.Cl.C(=O)([O-])[O-].[Na+].[Na+]>CO.O.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:11][CH2:12][CH:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:14][CH2:15]2)=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 345002Methyl 1-(4-nitrophenyl)piperidine-4-carboxylate

Product 1

HCID 45496772HCID 45496772, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
65 °C

Procedure

To a mixture of methyl 1-(4-nitrophenyl)piperidine-4-carboxylate (3.80 g) and iron powder (3.20 g) in methanol/water (40 mL/10 mL) was added conc. hydrochloric acid (2 mL) at room temperature. The reaction mixture was stirred at 65° C. for 3 hr. The reaction mixture was adjusted to pH=9 with saturated sodium carbonate, and the insoluble substance was removed by the filtration. The filtrate was concentrated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give the title compound (3.20 g).

Workup

  1. customthe insoluble substance was removed by the filtration
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b77a42285a884b73af8c36b03058a2fd
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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