Potassium Carbonate → 1-(3-Butynyl)-4-benzylpiperidine

HRID 1279374Notes

Reaction equation

HRID 1279374 reaction equation
S([CH2:5][CH2:6][C:7]#[CH:8])(C)(=O)=O.[CH2:9]([CH:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:5]([N:19]1[CH2:20][CH2:21][CH:16]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:17][CH2:18]1)[CH2:6][C:7]#[CH:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 12053774192989-95-0

Product 1

HCID 106093551-(3-Butynyl)-4-benzylpiperidineYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesylbut-3-yne (3.03 g, 20.0 mmol), 4-benzylpiperidine (4.21 g, 24.0 mmol) and K2CO3 (8.28 g, 60.0 mmol) in 50 mL of CH3CN is refluxed for 12 hr. The mixture is filtered and washed with EtOAc (3×30 mL). The filtrate is evaporated in vacuo and is purified by flash chromatography to give the product as pale yellow oil (4.30 g, 95%): 1H NMR (CDCl3) 1.32 (m, 2 H), 1.51 (m, 1 H), 1.65 (m, 2 H), 1.94 (m, 3 H), 2.36 (m, 2 H), 2.54 (m, 4 H), 2.86 (d, J=11.4 Hz, 2 H), 7.12-7.27 (m, 5 H).

Workup

  1. temperatureis refluxed for 12 hr
  2. filtrationThe mixture is filtered
  3. washwashed with EtOAc (3×30 mL)
  4. customThe filtrate is evaporated in vacuo
  5. customis purified by flash chromatography

Sources & evidence

ORD record
ord-749d097cc9c64ff6b1492c8224322d97
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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