Triethylamine → N-[[4-(Tetradecyloxy)phenyl]methyl]benzamide

HRID 1728884Notes

Reaction equation

HRID 1728884 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=N[CH:4]=1.[CH2:11]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].[CH2:34](N(CC)CC)C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH2:11]([O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH:33][C:2](=[O:9])[C:3]2[CH:8]=[CH:7][CH:6]=[CH:34][CH:4]=2)=[CH:28][CH:27]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 516892Sodium BicarbonateHCID 117234984-(Tetradecyloxy)benzenemethanamine

Product 1

HCID 19015909N-[[4-(Tetradecyloxy)phenyl]methyl]benzamideYield 89.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a room temperature slurry of 2.01 g of nicotinoyl chloride hydrochloride in 25 ml of methylene chloride is added, via cannula, 3.0 g of product from Example 99 in 75 ml of methylene chloride. After 10 minutes, 3.8 g of triethylamine is added, dropwise, and the solution is stirred at room temperature for 20 hours. The reaction is poured into half saturated sodium bicarbonate and extracted with chloroform. The combined organic layers are washed with saturated sodium chloride and concentrated in vacuo. The residue is purified by chromatography (silica gel: 7.5% methyl alcohol/chloroform) and recrystallized from heptane/methyl alcohol to give 3.57 g of the desired product as pale yellow needles.

Workup

  1. extractionextracted with chloroform
  2. washThe combined organic layers are washed with saturated sodium chloride
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by chromatography (silica gel: 7.5% methyl alcohol/chloroform)
  5. customrecrystallized from heptane/methyl alcohol

Sources & evidence

ORD record
ord-c60d6f5d7cde42398b0e92ad1cb7f08f
Source dataset
uspto-grants-1994_07
Patent number
US05328921

Reaction notes

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