Hydrochloric Acid → Diethyl 4-(2-Aminoethoxy)pyridine-2,6-dicarboxylate Hydrochloride

HRID 2173754Notes

Reaction equation

HRID 2173754 reaction equation
C(OC([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:15]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:13]=1)=O)(C)(C)C.[ClH:28]>O1CCOCC1>[ClH:28].[NH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:15]=[C:14]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57570882Diethyl 4-(2-tert-butoxycarbonylamino-ethoxy)-pyridine-2,6-dicarboxylate

Product 1

HCID 66713944Diethyl 4-(2-Aminoethoxy)pyridine-2,6-dicarboxylate Hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 2.64 g of diethyl 4-(2-tert-butoxycarbonylamino-ethoxy)-pyridine-2,6-dicarboxylate (described on page 101 of WO 07085930) in 27 ml of dioxane was added 20.7 ml of 4N hydrochloric acid in dioxane. The mixture was stirred for about 20 hours at room temperature and then concentrated under reduced pressure. The evaporation residue was taken up in about 70 ml of dioxane, and then concentrated again under reduced pressure. The operation was repeated 3×. The mixture was taken up in 50 ml of tert-butyl methyl ether and the suspension obtained was filtered through a sinter of porosity 4. The cake was washed with tert-butyl methyl ether, and dried in a desiccator under reduced pressure at room temperature. 2 g of diethyl 4-(2-amino-ethoxy)-pyridine-2,6-dicarboxylate monohydrochloride were obtained. 1H NMR (400 MHz, DMSO-ds): 1.35 (t, J=7.2 Hz, 6H); 3.26 (m, 2H); 4.39 (q, J=7.2 Hz, 4H); 4.45 (m, 2H); 7.77 (s, 2H); 8.16 (broad m, 3H). LC/MS (C): tr=2.39 min; [M+H]+: m/z 283.

Workup

  1. concentrationconcentrated under reduced pressure
  2. concentrationconcentrated again under reduced pressure
  3. customthe suspension obtained
  4. filtrationwas filtered through a sinter of porosity 4
  5. washThe cake was washed with tert-butyl methyl ether
  6. customdried in a desiccator under reduced pressure at room temperature

Sources & evidence

ORD record
ord-35066c908c3b41818a9a50525c7e3797
Source dataset
uspto-grants-2015_06
Patent number
US09056914B2

Reaction notes

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