Hydrochloric Acid → HCID 59441766, compound

HRID 1014186Notes

Reaction equation

HRID 1014186 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][N:13]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:11][CH:10]=2)=[CH:5][C:4]=1[N+:18]([O-])=O.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:14][N:13]([CH2:15][CH2:16][CH3:17])[CH2:12][CH2:11][CH:10]=2)=[CH:5][C:4]=1[NH2:18]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59441903HCID 59441903, compound

Product 1

HCID 59441766HCID 59441766, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 5-[4-(methyloxy)-3-nitrophenyl]-1-propyl-1,2,3,6-tetrahydropyridine (0.25 g, 0.91 mmol) in absolute ethanol (50 mL) was added Sn2CL2×2H2O (1.22 g, 5.41 mmol, Aldrich) and a catalytic HCl (1 mL, 1M solution in dioxanes). After stirring overnight, the reaction was quenched with saturated sodium bicarbonate solution (50 mL), stirred at RT for 1 hr, solids removed by vacuum filtration through a celite pad and rinsed with methanol. The solvent was removed under reduced pressure, aqueous layer extracted with dichloromethane (2×50 mL), combined organic extracts adsorbed to silica gel and purified by silica gel chromatography (dichloromethane to 5% methanol/dichloromethane+0.1% NH4OH) to afford 2-(methyloxy)-5-(1-propyl-1,2,5,6-tetrahydro-3-pyridinyl)aniline (0.145 g, 65%). 1H NMR (400 MHz, CDCl3) δ ppm 0.94 (t, J=7.52 Hz, 3 H) 1.56-1.66 (m, 2 H) 2.28-2.36 (m, 2 H) 2.43-2.48 (m, 2 H) 2.58 (t, J=5.87 Hz, 2 H) 3.23-3.29 (m, 2 H) 3.84 (s, 3 H) 5.94-6.01 (m, 1 H) 6.68-6.76 (m, 3 H). ESIMS (M+H)+=247.

Workup

  1. customthe reaction was quenched with saturated sodium bicarbonate solution (50 mL)
  2. stirringstirred at RT for 1 hr
  3. customsolids removed by vacuum filtration through a celite pad
  4. washrinsed with methanol
  5. customThe solvent was removed under reduced pressure, aqueous layer
  6. extractionextracted with dichloromethane (2×50 mL)
  7. custompurified by silica gel chromatography (dichloromethane to 5% methanol/dichloromethane+0.1% NH4OH)

Sources & evidence

ORD record
ord-93e7532ec4cc443ebfb4321850103722
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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