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

HRID 84352

Reaction equation

HRID 84352 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][C:22]([CH3:25])=[C:21]([CH3:26])[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][C:22]([CH3:25])=[C:21]([CH3:26])[CH:20]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 114173,4-DimethylpyridineHCID 108519404-(5-Bromopentyl)-1,1'-biphenyl

Product 1

HCID 247816841-[5-(1,1'-Biphenyl-4-yl)-pentyl]-3,4-dimethyl-pyridinium bromideYield 87%

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(5-bromopentyl)-1,1′-biphenyl (322 mg, 1.06 mmol) and 3,4-lutidine (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 380 mg of the title compound. Yield: 87%. 1H NMR (300 MHz, CDCl3) δ 1.43 (m, 2H), 1.69 (m, 2H), 2.05 (m, 2H), 2.46 (s, 3H), 2.48 (s, 3H), 2.62 (t, J=7.5 Hz, 2H), 4.82 (t, J=7.2 Hz, 2H), 7.18-7.58 (m, 9H), 7.76 (d, J=6.3 Hz, 1H), 9.07 (d, J=6.3 Hz, 1H), 9.29 (s, 1H) ppm; 13C NMR (75 MHz, CDCl3) δ 17.1, 20.4, 25.6, 30.7, 31.7, 35.2, 60.7, 126.8, 126.9, 127.0, 128.4, 128.7, 128.8, 138.2, 138.5, 140.7, 141.1, 141.7, 143.3, 157.4 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-425cdf00fce64c97932e19bc38db9e90
Source dataset
uspto-grants-2014_09
Patent number
US08846937B2

Linked notes

Loading…