Potassium Carbonate → HCID 18427961, compound

HRID 366519Notes

Reaction equation

HRID 366519 reaction equation
[CH3:1][C:2]1[CH:18]=[CH:17][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([CH:13](C)[C:14]#[CH:15])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.[CH3:20][C:21]1[CH:33]=[CH:32][C:24](CN2CCCCC2)=[CH:23][CH:22]=1.C#CC(CS([O-])(=O)=[O:40])C.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][CH2:14][C:15]#[C:20][C:21]3[CH:33]=[CH:32][C:24]([OH:40])=[CH:23][CH:22]=3)[CH2:11][CH2:12]2)=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 18427926HCID 18427926, compoundHCID 18427996HCID 18427996, compoundHCID 19042311HCID 19042311, compound

Product 1

HCID 18427961HCID 18427961, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(4-Methylbenzyl)-1-(1-butyn-3-yl)piperidine. A mixture of 4-methylbenzylpiperidine hydrochloride (1.129 g, 5.0 mmol), 1-butyn-3-ylmethanesulfonate (0.888 g, 5.0 mmol), and potassium carbonate (2.48 g, 12.5 mmol) in 30 mL of acetonitrile is heated to reflux for 12 hr. The inorganic salt is removed through a short column of silica gel and washed with ethyl acetate (3×30 mL). Evaporation of solvents gives a residue, which is purified by flash chromatography (50% EtOAc in hexane), giving 0.96 g (80%) of the title compound as pale yellow oil. 1H NMR (CDCl3) 1.26 (m, 3 H), 1.50 (m, 1 H), 1.61 (m, 2 H), 1.96 (m, 2 H), 2.31 (s, 3 H), 2.36 (m, 2 H), 2.47-2.59 (m, 4 H), 2.86 (d, J=11.4 Hz, 2 H), 7.07 (dd, J1==7.8 Hz, J2=10.5 Hz, 4 H).

Workup

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

Sources & evidence

ORD record
ord-8d5740d6d4e246768548a5e707455a90
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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