Ethyl Nicotinate → HCID 20062134, compound

HRID 1085381Notes

Reaction equation

HRID 1085381 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH2:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[C:31]([O:39][CH2:40][CH3:41])(=[O:38])[C:32]1[CH:37]=[CH:36][CH:35]=[N:34][CH:33]=1>CCOCC>[Br-:1].[CH2:13]([O:12][CH2:11][CH2:10][CH2:9][O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N+:34]1[CH:35]=[CH:36][CH:37]=[C:32]([C:31]([O:39][CH2:40][CH3:41])=[O:38])[CH:33]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]

Participants

4

Reactant 2

HCID 69188Ethyl NicotinateHCID 200621241-Bromo-6-[3-(octadecyloxy)propoxy]hexane

Product 1

HCID 20062134HCID 20062134, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

1-Bromo-6-[3-(octadecyloxy)propoxy]hexane obtained in Reference Example 4 (1.0 g) is heated with ethyl nicotinate (0.66 g) at 90° C. for 19 hours. After the reaction mixture is cooled, ether is added to the reaction mixture and the precipitate is collected by filtration to give 1-N-[6-[3-(octadecyloxy)propoxy]-hexyl]-3-ethoxycarbonylpyridinium bromide (1.0 g). To this compound in methanol (25 ml) is added with stirring 2N sodium hydroxide (4 ml), and the mixture is stirred at room temperature for 20 minutes. The reaction mixture is neutralized with 1 N hydrochloric acid, concentrated under reduced pressure, and extracted with dichloromethane. The extract is washed with an aqueous solution saturated with sodium chloride, dried and concentrated. The residue is subjected to purification by means of silica gel chromatography (chloroform-methanol-water= 65:25:4) and then to reprecipitation from chloroform-acetone to give the above-titled compound as pale yellow powder (0.63 g).

Workup

  1. temperatureAfter the reaction mixture is cooled
  2. filtrationthe precipitate is collected by filtration

Sources & evidence

ORD record
ord-d9655df2ae224887bdc53314b7e89b74
Source dataset
uspto-grants-1991_04
Patent number
US05008454

Reaction notes

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