3,5-Bis(trifluoromethyl)benzylamine → n-(3,5-Bis-trifluoromethyl-benzyl)-3-o-tolyl-isonicotinamide

HRID 1975960Notes

Reaction equation

HRID 1975960 reaction equation
[C:1]1([CH3:16])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[CH:15]=[N:14][CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=O.[F:17][C:18]([F:32])([F:31])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:22][NH2:23].Cl.CN(C)CCCN=C=NCC>ClCCl>[F:17][C:18]([F:31])([F:32])[C:19]1[CH:20]=[C:21]([CH:24]=[C:25]([C:27]([F:30])([F:28])[F:29])[CH:26]=1)[CH2:22][NH:23][C:9](=[O:11])[C:8]1[CH:12]=[CH:13][N:14]=[CH:15][C:7]=1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:16]

Participants

5

Reactant 3

HCID 5210993,5-Bis(trifluoromethyl)benzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 220000663-(2-Methylphenyl)-4-pyridinecarboxylic acid

Product 1

HCID 22000068n-(3,5-Bis-trifluoromethyl-benzyl)-3-o-tolyl-isonicotinamideYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.28 g (1.17 mol) 3-o-tolyl-isonicotinic acid and 0.34 g (1.40 mmol) 3,5-bis(trifluoromethyl)benzylamine in 10 ml dichloromethane 0.38 ml N-methylmorpholine and 0.27 g (1.40 mmol) N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimide hydrochloride were added and the mixture stirred for 12 h. The phases were separated, the water phase extracted with three portions of dichloromethane. The combined organic phases were dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.26 g (51%) of the title compound as a colorless oil.

Workup

  1. customThe phases were separated
  2. extractionthe water phase extracted with three portions of dichloromethane
  3. dry with materialThe combined organic phases were dried (magnesium sulfate)
  4. customevaporated

Sources & evidence

ORD record
ord-eece56e977e84d8884747d6be26836bf
Source dataset
uspto-grants-2001_05
Patent number
US06225316B1

Reaction notes

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