1-Butanol → N,N-Diethylnicotinamide

HRID 1605962Notes

Reaction equation

HRID 1605962 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:10]([NH:12][CH2:13][CH3:14])[CH3:11].C1(C)C=CC=CC=1.C(O)CCC>C(O[Ti](OCCCC)(OCCCC)OCCCC)CCC.O>[CH3:11][CH2:10][N:12]([C:1]([C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1)=[O:9])[CH2:13][CH3:14]

Participants

7

Reactant 4

HCID 2631-ButanolHCID 938Nicotinic AcidHCID 1140TolueneHCID 8021Diethylamine

Product 1

HCID 5497N,N-Diethylnicotinamide

Reagents, catalysts & solvents 2

HCID 178454852HCID 178454852, compoundCatalystHCID 962WaterSolvent

Procedure

Nicotinic acid (0.5 mole), diethylamine (0.5 mole), toluene (35 ml), n-butanol (60 ml) and tetra n-butoxy titanium were heated until all water was removed by azeotropic distillation from the reaction mixture. The volatile solvents were then distilled off and the remaining product fractionally distilled under vacuum to give nikethamide identified both by its boiling point and its infra-red spectrum.

Workup

  1. customwas removed by azeotropic distillation from the reaction mixture
  2. distillationThe volatile solvents were then distilled off
  3. distillationthe remaining product fractionally distilled under vacuum

Sources & evidence

ORD record
ord-56f7dd3d2c1041b2b2dd4df22fb8bee3
Source dataset
uspto-grants-1976_04
Patent number
US03951996

Reaction notes

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