Potassium Carbonate → 4-Phenyl-1-(4-phenyl-3-butynyl)piperidine

HRID 1279369Notes

Reaction equation

HRID 1279369 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.[C:15]1([CH:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[C:15]1([CH:21]2[CH2:22][CH2:23][N:24]([CH2:5][CH2:6][C:7]#[C:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:25][CH2:26]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 698734-PhenylpiperidineHCID 184279661-Mesyl-4-phenylbut-3-yne

Product 1

HCID 184279594-Phenyl-1-(4-phenyl-3-butynyl)piperidineYield 48.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-mesyl-4-phenylbut-3-yne (200 mg, 0.870 mmol), 4-phenylpiperidine (120 mg, 0.744 mmol) and K2CO3 (308 mg, 2.23 mmol) in 10 mL of CH3CN 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 (104 mg, 41%): mp 65-66° C.; 1H NMR (CDCl3) 1.81 (m, 4 H), 2.26 (m, 2 H), 2.65 (m, 1 H), 2.69 (m, 2 H), 2.76 (m, 2 H), 3.13 (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-3a01f8e5b97543b2b8c8d528f5e167a7
Source dataset
uspto-grants-2002_09
Patent number
US06448270B1

Reaction notes

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