Hydrochloric Acid → 1-[5-(Aminomethyl)-2-pyridinyl]-3,3-dimethyl-1-butanone

HRID 2041482Notes

Reaction equation

HRID 2041482 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:23])[CH2:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N:15][CH:16]=1)=O)(C)(C)C>O1CCOCC1.ClCCl>[NH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:23])[CH2:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[N:15][CH:16]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 57656622HCID 57656622, compound

Product 1

HCID 576565211-[5-(Aminomethyl)-2-pyridinyl]-3,3-dimethyl-1-butanoneYield 88.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (1 mL) to a solution of 5-tert-butoxycarbonylaminomethyl-2-(3,3-dimethyl-butyryl)-pyridine (104 mg, 0.339 mmol) in anhydrous dichloromethane (4 mL) and stir the solution overnight. Concentrate in vacuo and partition the residue between saturated aqueous NaHCO3 and dichloromethane. Extract the aqueous phase with dichloromethane (2×15 mL) and EtOAc (2×15 mL). Dry the combined organic extracts over Na2SO4, filter and concentrate in vacuo to obtain the title compound as an oil (62 mg, 88%) that was used without any further purification. MS (ES+) m/z: 207 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition the residue between saturated aqueous NaHCO3 and dichloromethane
  3. extractionExtract the aqueous phase with dichloromethane (2×15 mL) and EtOAc (2×15 mL)
  4. dry with materialDry the combined organic extracts over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-04d6e3cc09f64612ba5d579cc8a09e65
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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