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

HRID 1110801Notes

Reaction equation

HRID 1110801 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.

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-0095119e48a24fe6b37febb52e31df7c
Source dataset
uspto-grants-1990_12
Patent number
US04977170

Reaction notes

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