Methylamine → 3-Aminomethyl-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octane

HRID 1693053Notes

Reaction equation

HRID 1693053 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:8]2[C:13](=O)[CH:12]3[CH2:15][CH2:16][N:9]2[CH2:10][CH2:11]3)[CH:2]=1.CN.[C:19]([BH3-])#[N:20].[Na+].[OH-].[K+]>[Cl-].[Zn+2].[Cl-].CO>[NH2:20][CH2:19][CH:13]1[CH:12]2[CH2:15][CH2:16][N:9]([CH2:10][CH2:11]2)[CH:8]1[CH2:7][C:3]1[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 6329MethylamineHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 102200302-(Pyridin-3-ylmethyl)quinuclidin-3-one

Product 1

HCID 223113793-Aminomethyl-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octaneYield 83%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

2-((3-Pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one (2.16 g, 0.01 mol), methylamine (25 mL, 0.05 mol) and zinc chloride (5 mL, 0.005 mol) were added to dry methanol (30 mL) and stirred at room temperature for 30 min. Then, sodium cyanoborohydride (30 mL, 1.0M in THF) was added carefully and the mixture stirred at room temperature for 48 h. The mixture was adjusted to pH 10 using 2N potassium hydroxide and then the solvent was removed by rotary evaporation. The residue was extracted with chloroform (3×50 mL), dried (MgSO4), filtered and concentrated by rotary evaporation to yield the crude desired amine as a light yellow oil (2.40 g, 83% yield). The product was taken on to the next step without further purification.

Workup

  1. stirringthe mixture stirred at room temperature for 48 h
  2. customthe solvent was removed by rotary evaporation
  3. extractionThe residue was extracted with chloroform (3×50 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-76b2b9962cfe481b96db0d229d2b2d0b
Source dataset
uspto-grants-2012_04
Patent number
US08158649B2

Reaction notes

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