Hydrochloric Acid → 6-(Methylamino)-2-pyridylethanol

HRID 1815982Notes

Reaction equation

HRID 1815982 reaction equation
C(OC([CH2:8][NH:9][C:10]1[N:15]=[C:14]([CH:16]([OH:18])[CH3:17])[CH:13]=[CH:12][CH:11]=1)=O)(C)(C)C.Cl>O1CCOCC1>[CH3:8][NH:9][C:10]1[N:15]=[C:14]([CH:16]([OH:18])[CH3:17])[CH:13]=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 224960276-[(tert-Butoxycarbonyl)methylamino]-2-pyridylethanol

Product 1

HCID 223194656-(Methylamino)-2-pyridylethanolYield 85%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 6-[(tert-butoxycarbonyl)methylamino]-2-pyridylethanol (17.9 g, 71 mmole) was added a solution of 4N HCl in dioxane (200 mL). The reaction was stirred at room temperature for 1 h (gentle gas evolution was observed) then was concentrated to dryness. The product as the hydrochloride salt solidified under vacuum. The solid was dissolved in NaCl-saturated 1.0 N NaOH solution (75 mL), and the solution was extracted with Et2O (2×200 mL). The combined organic layers were washed with brine, dried (Na2SO4), and concentrated to afford the title compound (9.12 g, 85%) as a waxy solid: 1H NMR (400 MHz, CDCl3) δ 7.37 (t, 1 H). 6.42 (d, J=7.3 Hz, 1 H), 6.27 (d, J=8.3 Hz, 1 H), 4.62 (br s, 1H), 3.96 (t, 2H). 2.90 (d, J=5.2 Hz, 3H), 2.84 (t, 2H); MS (ES) m/e 153 (M+H)+.

Workup

  1. concentrationthen was concentrated to dryness
  2. dissolutionThe solid was dissolved in NaCl-saturated 1.0 N NaOH solution (75 mL)
  3. extractionthe solution was extracted with Et2O (2×200 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9fb99eb3217f4820808e83723aed6285
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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