Hydrochloric Acid → 3-Aminomethyl-6-cyclohexylmethyl-pyridine

HRID 911663Notes

Reaction equation

HRID 911663 reaction equation
Cl.C(OC([NH:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:15][CH:16]=1)=O)(C)(C)C.CCCCCC>O1CCOCC1.CCOC(C)=O>[NH2:9][CH2:10][C:11]1[CH:12]=[N:13][C:14]([CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 576559013-Tert-butoxycarbonylaminomethyl-6-cyclohexylmethyl-pyridine

Product 1

HCID 576566033-Aminomethyl-6-cyclohexylmethyl-pyridineYield 97%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Add 4N hydrogen chloride in dioxane (10 mL) to a solution of 3-tert-butoxycarbonylaminomethyl-6-cyclohexylmethyl-pyridine (345 mg, 1.13 mmol) in EtOAc (10 mL) and stir overnight Concentrate in vacuo, suspend the solid obtained in diethyl ether and add hexane. Filter and wash the solid with hexane. Suspend the solid into dichloromethane, add saturated aqueous NaHCO3 and stir until both phases are clear (15 min). Extract the aqueous phase twice with dichloromethane. Dry the combined organic extracts over MgSO4, filter and concentrate in vacuo to obtain the title compound as an oil (205 mg, 97%) that was used without any further purification. MS (ES+) m/z: 205 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. customobtained in diethyl ether
  3. filtrationFilter
  4. washwash the solid with hexane
  5. additionadd saturated aqueous NaHCO3
  6. stirringstir until both phases
  7. custom(15 min)
  8. extractionExtract the aqueous phase twice with dichloromethane
  9. dry with materialDry the combined organic extracts over MgSO4
  10. filtrationfilter
  11. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-21c46941745541b1be412334c9b253f2
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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