4-Butylpyridine → 1-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3-butyl-pyridinium bromide

HRID 84356Notes

Reaction equation

HRID 84356 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.C([C:23]1[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=1)CCC>>[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+:26]2[CH:25]=[CH:24][CH:23]=[C:28]([CH2:2][CH2:3][CH2:4][CH3:5])[CH:27]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 1384594-ButylpyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

Product 1

HCID 247818231-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3-butyl-pyridinium bromideYield 72%

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (360 mg, 1.19 mmol) and 4-n-butylpyridine (0.5 mL) was heated at 60-70° C. for 12 hrs. The resulting mixture was washed with diethyl ether and then dissolved in water (15 mL). The aqueous solution was extracted with ethyl acetate (30 mL×3). Water was removed by lyophilization to afford 377 mg of the title compound. Yield: 72%. 1H NMR (300 MHz, CDCl3) δ 0.92 (t, J=7.2 Hz, 3H), 1.29-1.53 (m, 4H), 1.60-1.80 (m, 4H), 2.08 (m, 2H), 2.63 (t, J=7.5 Hz, 2H), 2.85 (t, J=7.8 Hz, 2H), 4.94 (t, J=7.5 Hz, 2H), 7.18-7.60 (m, 9H), 8.00 (t, J=7.2 Hz, 1H), 8.16 (d, J=8.1 Hz, 1H), 9.29 (d, J=6.0 Hz, 1H), 9.30 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 13.9, 22.3, 25.7, 30.8, 32.0, 32.5, 32.6, 35.2, 61.7, 126.8, 127.0, 127.1, 128.0, 128.8, 128.9, 138.6, 140.8, 141.1, 142.5, 144.0, 144.1, 144.6 ppm.

Workup

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

Sources & evidence

ORD record
ord-20fe6ea57a354910a88a120b7c3de2f7
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Reaction notes

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