Triethylamine → N-[(4-Cyanophenyl)methyl]nonanamide

HRID 622409Notes

Reaction equation

HRID 622409 reaction equation
[NH2:1][CH2:2][C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:18](Cl)(=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]>C(Cl)(Cl)Cl>[C:7]([C:6]1[CH:9]=[CH:10][C:3]([CH2:2][NH:1][C:18](=[O:27])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])=[CH:4][CH:5]=1)#[N:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69819Nonanoyl chlorideHCID 826084-(Aminomethyl)benzonitrile

Product 1

HCID 15725465N-[(4-Cyanophenyl)methyl]nonanamideYield 98.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 4-(aminomethyl)benzonitrile (5.0 g, 0.038 moles) in 100 mL chloroform is added 3.82 g (0.038 moles) triethylamine. A solution of nonanoyl chloride (6.68 g, 0.038 moles) in 10 mL chloroform is then added dropwise with stirring over a 10 min period and the final mixture stirred at room temperature for 18 hrs. The mixture is extracted with water (100 mL), saturated NaHCO3 (50 mL), 2N HCl (50 mL), dried over Na2SO4 and evaporated to leave 10.2 g crude N-(4-cyanobenzyl)nonanamide. This crude product is taken up in 50 mL dimethylformamide, to which is added 2.47 g (0.038 moles) sodium azide and 2.03 g (0.038 moles) ammonium chloride. The final mixture is heated at 90°-110° C. for 4 hrs after cooling, the mixture is diluted with water (350 mL) and the resultant precipitate recovered by suction filtration, washed with water, and vacuum dried. Recrystallization from ethyl acetate left N-[[4-(1H-tetrazol-5-yl)phenyl]methyl]nonanamide (2.6 g), m.p. 185°-187° C.

Workup

  1. extractionThe mixture is extracted with water (100 mL), saturated NaHCO3 (50 mL), 2N HCl (50 mL)
  2. dry with materialdried over Na2SO4
  3. customevaporated

Sources & evidence

ORD record
ord-0707ad4721084ac1a5970badd8b8a762
Source dataset
uspto-grants-1988_09
Patent number
US04771064

Reaction notes

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