N-Methylbenzylamine → Benzyl-methyl-(2-pyridine-3-yl-ethyl-)amine

HRID 1351250Notes

Reaction equation

HRID 1351250 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9](O)=O)[CH:3]=1.[CH2:12]([NH:19][CH3:20])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>ClCCl.O1CCCC1.O.C(OCC)C.C(N(CC)CC)C>[CH2:12]([N:19]([CH3:20])[CH2:9][CH2:8][C:4]1[CH:3]=[N:2][CH:7]=[CH:6][CH:5]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

10

Reactant 4

HCID 7669N-MethylbenzylamineHCID 14798Sodium HydroxideHCID 27237243-Pyridineacetic acid, hydrochloride (1:1)HCID 21226445Aluminium lithium hydride

Product 1

HCID 21098723Benzyl-methyl-(2-pyridine-3-yl-ethyl-)amineYield 66.7%

Reagents, catalysts & solvents 5

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

To a solution of pyridine-3-yl-acetic acid hydrochloride (5 g), benzyl-methyl-amine (3.5 g), and benzotriazole-1-yloxytris-hydroxymethyl-aminomethane(dimethylamino) phosphonium hexafluorophosphate (14 g) in dichlorometan (50 mL) was added triethylamine (8.8 mL). After this solution was stirred for 15 minutes, the residue from the evaporation of the solvent at reduced pressure was purified by silica gel column chromatography (hexane/ethyl acetate), and a colorless oily matter was obtained. This oily substance was dissolved in a tetrahydrofuran solution (60 mL), added dropwise into an anhydrous tetrahydrofuran (300 mL) in which lithium aluminum hydride (2.1 g) was suspended, and stirred for 1 hour. To the reaction solution was added diethyl ether (60 mL), water (2.1 mL), an aqueous solution (2.1 mL) of 15% sodium hydroxide and water (6.3 mL). After stirring for 30 minutes, the resulting solid was removed by filtration, the residue from the removal of the solvent by evaporation was purified by NH silica gel column chromatography (hexane/ethyl acetate), and the oily residue (4.35 g) was obtained.

Workup

  1. customthe residue from the evaporation of the solvent at reduced pressure
  2. customwas purified by silica gel column chromatography (hexane/ethyl acetate)
  3. customa colorless oily matter was obtained
  4. stirringstirred for 1 hour
  5. stirringAfter stirring for 30 minutes
  6. customthe resulting solid was removed by filtration
  7. customthe residue from the removal of the solvent
  8. customby evaporation
  9. customwas purified by NH silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-a6bdbb3e59d3401585903afe54ec4edd
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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