Potassium Carbonate → 4-(4-Methylbenzyl)-4-hydroxy-1-(but-3-yn-1-yl)piperidine

HRID 366523Notes

Reaction equation

HRID 366523 reaction equation
CC1(O)C=C[C:5]([CH2:6][N:7]2[CH2:12][CH2:11]C[CH2:9][CH2:8]2)=[CH:4][CH2:3]1.CS(O[CH2:21][CH2:22][C:23]#[CH:24])(=O)=O.[C:25](=[O:28])([O-])[O-].[K+].[K+]>C(#N)C>[CH3:21][C:22]1[CH:3]=[CH:4][C:5]([CH2:6][C:25]2([OH:28])[CH2:9][CH2:8][N:7]([CH2:6][CH2:5][C:4]#[CH:3])[CH2:12][CH2:11]2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11378578But-3-yn-1-yl methanesulfonateHCID 699498874-Methyl-4-hydroxybenzylpiperidine

Product 1

HCID 107536454-(4-Methylbenzyl)-4-hydroxy-1-(but-3-yn-1-yl)piperidineYield 65%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-methyl-4-hydroxybenzylpiperidine hydrocholoride (1.3 g, 5.4 mmol), 1-butyn-4-yl methanesulfonate (0.96 g, 6.5 mmol), potassium carbonate (2.5 g, 18 mmol) in 50 mL of acetonitrile was allowed to reflux for 12 hrs. The inorganic salt was removed through a short column of silica gel and washed with ethyl acetate (3×30 mL). Evaporation of solvents gave a residue, which was purified by flash chromatography (50% EtOAc in hexane), giving 0.90 g (65%) of the title compound as a pale yellow oil. 1H NMR (CDCl3) 1.258 (m, 2 H), 1.883 (m, 2 H), 1.962 (m, 3 H), 2.040 (m, 2 H), 2.342 (s, 3 H), 2.399 (m, 2 H), 2.611 (m, 3 H), 2.708 (m, 2 H), 7.060-7.135 (m, 4 H).

Workup

  1. temperatureto reflux for 12 hrs
  2. customThe inorganic salt was removed through a short column of silica gel
  3. washwashed with ethyl acetate (3×30 mL)
  4. customEvaporation of solvents
  5. customgave a residue, which
  6. customwas purified by flash chromatography (50% EtOAc in hexane)

Sources & evidence

ORD record
ord-0dee7541fac5412496d861e7c841913c
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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