Potassium Carbonate → HCID 18621499, compound

HRID 1861786Notes

Reaction equation

HRID 1861786 reaction equation
[C:1]([O:9][CH2:10][C:11]#[C:12][CH2:13]Br)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:1]([O:9][CH2:10][C:11]#[C:12][CH2:13][N:25]1[CH2:26][CH2:27][CH:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][CH2:24]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 11747137HCID 11747137, compound

Product 1

HCID 18621499HCID 18621499, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-benzoyloxy-4-bromobut-2-yne (1.26 g, 5.00 mmol), 4-benzylpiperidine (0.964 g, 5.50 mmol) and K2CO3 (1.52 g, 11.0 mmol) in 50 mL of CH3CN was refluxed under N2 for 24 hr. The inorganic salt was removed through a short column of silica gel and was washed with EtOAc (3×30 mL). The filtrate was evaporated in vacuo to give a residue, which was purified by flash chromatography to give the product as a brown oil (0.55 g, 32%): 1H NMR (CDCl3) d 1.34 (m, 2 H), 1.50 (m, 1 H), 1.63 (m, 2 H), 2.11 (m, 2 H), 2.51 (d, J=6.9 Hz, 2 H), 2.78 (m, 2 H), 2.86 (d, J=11.1 Hz, 2 H), 3.31 (s, 2 H), 4.94 (s, 2 H), 7.12-7.52 (m, 8 H); MS (m/z) 348 (M++1, 20), 347 (M+, 100), 346 (M+−1, 60), 226 (30), 105 (100).

Workup

  1. temperaturewas refluxed under N2 for 24 hr
  2. customThe inorganic salt was removed through a short column of silica gel
  3. washwas washed with EtOAc (3×30 mL)
  4. customThe filtrate was evaporated in vacuo
  5. customto give a residue, which
  6. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-961ab6a5c6284e5abf136a454a36d55f
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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