p-Xylyl bromide → 1-(4-Methylbenzyl)piperidin-4-ol

HRID 1291172Notes

Reaction equation

HRID 1291172 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13]Br)=[CH:11][CH:10]=1.C(N(CC)CC)C>CN(C)C=O>[CH3:8][C:9]1[CH:16]=[CH:15][C:12]([CH2:13][N:5]2[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 7721p-Xylyl bromideHCID 8471TriethylamineHCID 79341Piperidin-4-ol

Product 1

HCID 7914821-(4-Methylbenzyl)piperidin-4-olYield 482.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.15 g (0.00114 mol) of 4-hydroxypiperidine were dissolved in 15 ml of dimethylformamide and cooled to 0°. 1.92 g (0.001037 mol) of 4-methylbenzyl bromide and 1.59 ml (0.0114 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 dichloromethane/methanol (9:1) as the eluent. 1.028 g (48%) of 1-(4-methyl-benzyl)-piperidin-4-ol were obtained as beige crystals; m.p. 72°-74°.

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 dichloromethane/methanol (9:1) as the eluent

Sources & evidence

ORD record
ord-c778b9e527f24a1cb8122dcaa4fa1fce
Source dataset
uspto-grants-1998_05
Patent number
US05753679

Reaction notes

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