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

HRID 911618Notes

Reaction equation

HRID 911618 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-f86eda94172443b0a8e562cf00d2eae3
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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