Nicotinic Acid → N-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)nicotinamide

HRID 1199427Notes

Reaction equation

HRID 1199427 reaction equation
[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3][CH2:4][NH2:5].[C:17](O)(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1.[I-].ClC1C=CC=C[N+]=1C.CCN(CC)CC>C(Cl)Cl>[CH3:1][C:2]([CH2:6][CH2:7][CH:8]=[C:9]([CH3:16])[CH2:10][CH2:11][CH:12]=[C:13]([CH3:15])[CH3:14])=[CH:3][CH2:4][NH:5][C:17](=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[N:20][CH:19]=1

Participants

6

Reactant 4

HCID 938Nicotinic AcidHCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 3080630Farnesylamine2×

Product 1

HCID 85593820N-(3,7,11-Trimethyl-2,6,10-dodecatrienyl)nicotinamideYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2 mmol of N-(3,7,11-trimethyl-2,6,10-dodecatrienyl)amine (hereinafter abbreviated as farnesylamine), 2.2 mmol of nicotinic acid, 562 mg (2.2 mmol) of 2-chloro-1-methylpyridinium iodide, and 444 mg (4.4 mmol) of Et3N in 20 ml of CH2Cl2 is heated with stirring for 3 hours. The reaction mixture is washed twice with 20 ml of saturated aqueous NaHCO3 and twice with 20 ml of water. The mixture is dried and evaporated under reduced pressure. The residual oil is purified by silica-gel column chromatography and eluted with AcOEt to give 426 mg of the titled compound I-85. Yield: 65.2%.

Workup

  1. temperatureis heated
  2. washThe reaction mixture is washed twice with 20 ml of saturated aqueous NaHCO3 and twice with 20 ml of water
  3. customThe mixture is dried
  4. customevaporated under reduced pressure
  5. customThe residual oil is purified by silica-gel column chromatography
  6. washeluted with AcOEt

Sources & evidence

ORD record
ord-417e35cc41c44534b3cfc87fad13b19b
Source dataset
uspto-grants-1990_02
Patent number
US04900749

Reaction notes

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