Methyl iodide → 4-(1,2,5,6-Tetrahydro-1-methyl-3-pyridinyl)benzenemethanol

HRID 1784662Notes

Reaction equation

HRID 1784662 reaction equation
[CH3:1]I.[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]2[CH:16]=[CH:15][C:12]([CH:13]=[O:14])=[CH:11][CH:10]=2)[CH:4]=1.[BH4-].[Na+]>ClCCl>[OH:14][CH2:13][C:12]1[CH:15]=[CH:16][C:9]([C:5]2[CH2:4][N:3]([CH3:1])[CH2:8][CH2:7][CH:6]=2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 36930464-(Pyridin-3-yl)benzaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 671173834-(1,2,5,6-Tetrahydro-1-methyl-3-pyridinyl)benzenemethanolYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl iodide (0.8 ml, 12.9 mmol) was added to a solution of 4-(3-pyridyl)benzaldehyde (0.78 g, 4.3 mmol) in dichloromethane and stirred 2 days. Additional methyl iodide (0.8 ml, 12.9 mmol) was added and stirred for 3 hr. After removal of the solvent, methanol was added to the residue and ice-cooled. Sodium tetrahydroborate (6.4 g, 17.0 mmol) was added to the solution and stirred for 1.5 hr with warming to room temperature. Organic solvents were removed under reduced pressure after addition of water and extracted with ethyl acetate, washed with water and brine and dried over sodium sulfate. After removal of the solvent under reduced pressure, residue was purified by silica gel chromatography (eluent ethyl acetate to methanol) to give 3-(4-hydroxymethylphenyl)-1-methyl-1,2,5,6-tetrahydropyridine (0.63 g, 72%).

Workup

  1. stirringstirred for 3 hr
  2. customAfter removal of the solvent, methanol
  3. additionwas added to the residue and ice-
  4. temperaturecooled
  5. stirringstirred for 1.5 hr
  6. customOrganic solvents were removed under reduced pressure
  7. additionafter addition of water
  8. extractionextracted with ethyl acetate
  9. washwashed with water and brine
  10. dry with materialdried over sodium sulfate
  11. customAfter removal of the solvent under reduced pressure, residue
  12. customwas purified by silica gel chromatography (eluent ethyl acetate to methanol)

Sources & evidence

ORD record
ord-4a443f0ff195436fbdf1639a06c2e660
Source dataset
uspto-grants-2009_03
Patent number
US07504411B2

Reaction notes

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