Triethylamine → 1-[(4-Methoxyphenyl)methyl]-4-piperidinol

HRID 1291176Notes

Reaction equation

HRID 1291176 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14]Br)=[CH:12][CH:11]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79341Piperidin-4-olHCID 1650214-Methoxybenzyl bromide

Product 1

HCID 100137731-[(4-Methoxyphenyl)methyl]-4-piperidinolYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.97 g (0.00959 mol) of 4-hydroxypiperidine was dissolved in 20 ml of dimethylformamide and cooled to 0°. 1.93 g (0.0096 mol) of 4-methoxybenzyl bromide and 3.0 ml (0.0215 mol) of triethylamine were added under argon and the mixture was left to come to room temperature. It was stirred for 18 hrs., the solvent was distilled off and the residue was taken up in ethyl acetate. The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated and the residue was chromatographed on silica gel with dicloromethane/methanol (19:1) as the eluent. 1.7 g (80%) of 1-(4-methoxy-benzyl)-piperidin-4-ol were obtained as a brown oil. MS: me/e=222 (C13H20NO2+).

Workup

  1. temperaturecooled to 0°
  2. waitthe mixture was left
  3. customto come to room temperature
  4. distillation, the solvent was distilled off
  5. washThe organic phase was washed with water and saturated sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customthe residue was chromatographed on silica gel with dicloromethane/methanol (19:1) as the eluent

Sources & evidence

ORD record
ord-300dc818d6cd4b4985990f10699d3b30
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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