Potassium Carbonate → 5-Heptyl-2-[4-(8-cyclopentyl-octyloxy)-phenyl]-pyridine

HRID 962354Notes

Reaction equation

HRID 962354 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=2)=[N:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].Br[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH:30]3[CH2:34][CH2:33][CH2:32][CH2:31]3)=[CH:16][CH:15]=2)=[N:12][CH:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1722345Phenol, 4-(5-heptyl-2-pyridinyl)-HCID 19083614HCID 19083614, compound

Product 1

HCID 190835415-Heptyl-2-[4-(8-cyclopentyl-octyloxy)-phenyl]-pyridineYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 0.157 g of 4-(5-heptyl-2-pyridyl)-phenol, 0.153 g of (8-bromooctyl)-cyclopentane, 6 ml of dimethylformamide and 0.24 g of finely powdered potassium carbonate was stirred at 55° C. for 3 hours. The reaction mixture was partitioned between water and diethyl ether. The organic phase was washed with water and with saturated sodium chloride solution, dried over magnesium sulphate, filtered and the filtrate was concentrated. Chromatography of the crude product (0.28 g) on 10 g of silica gel with hexane/ethyl acetate 37:3 (v/v) and two-fold recrystallization of the product-containing fractions from 3 ml of hexane each time gave 0.16 g of pure 5-heptyl-2-[4-(8-cyclopentyl-octyloxy)-phenyl]-pyridine; m.p. (C-SI) 38.3° C., SI -SC 56.9° C., cl.p. (SC -I) 72.6° C.

Workup

  1. customThe reaction mixture was partitioned between water and diethyl ether
  2. washThe organic phase was washed with water and with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customChromatography of the crude product (0.28 g) on 10 g of silica gel with hexane/ethyl acetate 37:3 (v/v) and two-fold recrystallization of the product-containing fractions from 3 ml of hexane each time

Sources & evidence

ORD record
ord-6fc26b9f8f4e406ea5862185494fb5b6
Source dataset
uspto-grants-1998_06
Patent number
US05759443

Reaction notes

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