Hydrochloric Acid → (Z)-3-Aminomethyl-6-(2-cyclohexylvinyl)-pyridine

HRID 1190993Notes

Reaction equation

HRID 1190993 reaction equation
C(OC([NH:8][CH2:9][C:10]1[CH:11]=[N:12][C:13](/[CH:16]=[CH:17]\[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1)=O)(C)(C)C.Cl>CO>[NH2:8][CH2:9][C:10]1[CH:11]=[N:12][C:13](/[CH:16]=[CH:17]\[CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59828825(Z)-3-(tert-Butoxycarbonylamino-methyl)-6-(2-cyclohexylvinyl)-pyridine

Product 1

HCID 58495592(Z)-3-Aminomethyl-6-(2-cyclohexylvinyl)-pyridineYield 309.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Add (Z)-3-(tert-butoxycarbonylamino-methyl)-6-(2-cyclohexylvinyl)-pyridine (0.42 g, 1.33 mmol) to methanol (20 mL) and cool to 0° C. Bubble hydrogen chloride into the solution until saturated, and allow the mixture to warm to room temperature. Concentrate the mixture in vacuo and partition the residue between 3N aqueous NaOH (30 mL) and DCM (30 mL). Separate the layers and extract the aqueous phase with DCM (3×30 mL). Wash the combined organic extracts with brine (30 mL), dry over Na2SO4, filter, and concentrate in vacuo to obtain the title compound as a colorless oil (0.89 g, 80%). MS (APCI+) m/z: 217 (M+H)+.

Workup

  1. temperatureto warm to room temperature
  2. concentrationConcentrate the mixture in vacuo
  3. custompartition the residue between 3N aqueous NaOH (30 mL) and DCM (30 mL)
  4. customSeparate the layers
  5. extractionextract the aqueous phase with DCM (3×30 mL)
  6. washWash the combined organic extracts with brine (30 mL)
  7. dry with materialdry over Na2SO4
  8. filtrationfilter
  9. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-10143417d0694239a01a31a944e26d0f
Source dataset
uspto-grants-2014_03
Patent number
US08680091B2

Reaction notes

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