1,4-Dioxane hydrochloride → 1-(6-Methoxypyridin-3-yl)-2-(methylamino)ethanol dihydrochloride

HRID 23687Notes

Reaction equation

HRID 23687 reaction equation
[ClH:1].O1CCOCC1.[OH:8][CH:9]([C:20]1[CH:21]=[N:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=1)[CH2:10][N:11](C)[C:12](=O)OC(C)(C)C>CO>[ClH:1].[ClH:1].[CH3:27][O:26][C:23]1[N:22]=[CH:21][C:20]([CH:9]([OH:8])[CH2:10][NH:11][CH3:12])=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 22574350Tert-butyl 2-hydroxy-2-(6-methoxypyridin-3-yl)ethyl(methyl)carbamate

Product 1

HCID 225743691-(6-Methoxypyridin-3-yl)-2-(methylamino)ethanol dihydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of HCl-dioxane (4.0 M, 50 mL) was added tert-butyl 2-hydroxy-2-(6-methoxypyridin-3-yl)ethyl(methyl)carbamate (1.0 g, 3.5 mmol). The suspension was stirred at room temperature for 16 hours. The solvent and excess HCl was evaporated, leaving a white solid. The solid was dissolved in methanol and purified with a silica gel column, diluting with 1% NH4OH/5% Methanol/dichloromethane, to yield the title compound (0.63 g) as a colorless oil.

Workup

  1. customThe solvent and excess HCl was evaporated
  2. customleaving a white solid
  3. custompurified with a silica gel column
  4. additiondiluting with 1% NH4OH/5% Methanol/dichloromethane

Sources & evidence

ORD record
ord-32e910104abd4b838264237576a87f6d
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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