Hydrochloric Acid → 2-(5-Methoxypyridin-3-yl)ethanamine dihydrochloride

HRID 1749553Notes

Reaction equation

HRID 1749553 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH:11]C(=O)OC(C)(C)C)[CH:6]=[N:7][CH:8]=1.[ClH:19]>C(O)(C)C.O1CCOCC1>[ClH:19].[ClH:19].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[N:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131733599HCID 131733599, compound

Product 1

HCID 1181620852-(5-Methoxypyridin-3-yl)ethanamine dihydrochlorideYield 75%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (2-(5-methoxypyridin-3-yl)ethyl)carbamate (153 mg, 0.606 mmol) in isopropanol (2 mL) was added 4M HCl in dioxane (2 mL) and the mixture was stirred at room temperature for 16 h. The mixture was concentrated, the residual solid was washed with diethyl ether and dried in vacuum to provide the title compound as a white solid (103 mg, 0.458 mmol, 75%). 1H NMR (500 MHz, CD3OD): δ (ppm) 8.56 (d, J=2.52 Hz, 1H), 8.51 (s, 1H), 8.27 (s, 1H), 4.15 (s, 3H), 3.23-3.38 ppm (m, 4H).

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residual solid was washed with diethyl ether
  3. customdried in vacuum

Sources & evidence

ORD record
ord-3216a94490ca4da1a7555e6314fbec2d
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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