Potassium Carbonate → 4-Benzyl-1-(4-phenylbut-3-ynyl)piperidine

HRID 366511Notes

Reaction equation

HRID 366511 reaction equation
S([CH2:5][CH2:6][C:7]#[C:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)(C)(=O)=O.[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>[CH2:8]([CH:7]1[CH2:27][CH2:26][N:25]([CH2:24][CH2:23][C:22]#[C:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:5][CH2:6]1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 184279661-Mesyl-4-phenylbut-3-yne

Product 1

HCID 107095814-Benzyl-1-(4-phenylbut-3-ynyl)piperidineYield 38%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesyl-4-phenylbut-3-yne (200 mg, 0.87 mmol), 4-benzylpiperidine (175 mg, 1.00 mmol) and K2CO3 (368 mg, 2.67 mmol) in CH3CN (10 mL) is refluxed for 12 hr. The mixture is filtered and washed with EtOAc (3×15 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as an oil (100 mg, 38%): 1H NMR (CDCl3) 1.45 (m, 2 H), 1.52 (m, 1 H), 1.65 (m, 2 H), 2.05 (t, J=6.6 Hz, 2 H), 2.54 (m, 2 H), 2.68 (m, 4 H), 2.97 (d, J=11 Hz, 2 H), 7.13-7.36 (m, 10 H).

Workup

  1. temperatureis refluxed for 12 hr
  2. filtrationThe mixture is filtered
  3. washwashed with EtOAc (3×15 mL)
  4. customThe filtrate is evaporated in vacuo
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-c9f8440ef80a48e289d11ef6b0bc5c50
Source dataset
uspto-grants-2000_10
Patent number
US06130234

Reaction notes

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