Potassium Carbonate → HCID 18621463, compound

HRID 1861788Notes

Reaction equation

HRID 1861788 reaction equation
Br[CH2:2][C:3]#[C:4][CH3:5].[CH2:6]([CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+]>CC#N>[CH2:6]([CH:13]1[CH2:18][CH2:17][N:16]([CH2:2][C:3]#[C:4][CH3:5])[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 317384-BenzylpiperidineHCID 27568621-Bromo-2-butyne

Product 1

HCID 18621463HCID 18621463, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-bromobut-2-yne (1.19 g, 9.00 mmol), 4-benzylpiperidine (1.58 g, 9.00 mmol) and K2CO3 (2.5 g, 18 mmol) in 25 mL of CH3CN was refluxed for 12 hr. The mixture was filtered and was washed with EtOAc (3×30 mL). The filtrate was evaporated in vacuo and was purified by flash chromatography to give the product as a colorless oil (0.9 g, 50%): 1H NMR (CDCl3) d 1.31 (m, 2 H), 1.60 (m, 1 H), 1.63 (m, 2 H), 1.81 (s, 3 H), 2.04 (m, 2 H), 2.52 (d, J=9.9 Hz, 2 H), 2.88 (m, 2 H), 3.16 (s, 2 H), 7.15-7.27 (m, 5 H); HRMS calcd for C16H21N 227.1670, found 227.1670.

Workup

  1. temperaturewas refluxed for 12 hr
  2. filtrationThe mixture was filtered
  3. washwas washed with EtOAc (3×30 mL)
  4. customThe filtrate was evaporated in vacuo
  5. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-da8e5729d73841829d6057b0b4271ac0
Source dataset
uspto-grants-2003_03
Patent number
US06534522B2

Reaction notes

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