Pyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-pyridinium bromide

HRID 84357Notes

Reaction equation

HRID 84357 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[N:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[Br-:1].[C:10]1([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N+:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

Product 1

HCID 247818251-[5-(1,1'-Biphenyl-4-yl)-pentyl]-pyridinium bromideYield 90%

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (335 mg, 1.10 mmol) and pyridine (1 mL) was heated at 60-70° C. for 12 hrs. The resulted mixture was washed with diethyl ether and then dissolved in water (15 mL). The aqueous solution was extracted with diethyl ether (30 mL×3). Water was removed by lyophilization to afford 381 mg of the title compound. Yield: 90%. 1H NMR (300 MHz, CDCl3) δ 1.44 (m, 2H), 1.69 (m, 2H), 2.07 (m, 2H), 2.62 (t, J=7.5 Hz, 2H), 4.96 (t, J=7.5 Hz, 2H), 7.15-7.60 (m, 9H), 8.06 (t, J=6.9 Hz, 2H), 8.42 (d, J=7.8 Hz, 1H), 9.48 (d, J=6.0 Hz, 2H) ppm; 13C NMR (75 MHz, CDCl3) δ 25.6, 30.7, 31.9, 35.2, 61.8, 126.8, 127.0, 127.1, 128.4, 128.8, 128.9, 138.6, 140.8, 141.0, 145.0 ppm.

Workup

  1. washThe resulted mixture was washed with diethyl ether
  2. dissolutiondissolved in water (15 mL)
  3. extractionThe aqueous solution was extracted with diethyl ether (30 mL×3)
  4. customWater was removed by lyophilization

Sources & evidence

ORD record
ord-a4fa43411a434938907475b98616b05a
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

Loading…