4-Methoxybenzylamine → (4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-amine

HRID 1696744Notes

Reaction equation

HRID 1696744 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)[N:3]=1.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH2:29])=[CH:26][CH:25]=1>C(O)CCC>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:29][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([C:12]3[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=3)[N:3]=2)=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 754524-MethoxybenzylamineHCID 57468624HCID 57468624, compound

Product 1

HCID 57734027(4-Methoxy-benzyl)-[4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-amine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-bromo-4-trifluoromethyl-6-(4-trifluoromethyl-phenyl)-pyridine (5.55 g, 15 mmol) and 4-methoxybenzylamine (5.9 mL, 45 mmol) in n-butanol (15 mL) was refluxed for 2 days. Evaporated to dryness, diluted with EtOAc, washed with 5% citric acid, sat. NaHCO3-sol. and brine, dried over Na2SO4. Removal of the solvent in vacuum left the title compound as an orange oil (6.409 g, 100%). MS (ISP) 427.3 [(M+H)+].

Workup

  1. temperaturewas refluxed for 2 days
  2. customEvaporated to dryness
  3. additiondiluted with EtOAc
  4. washwashed with 5% citric acid, sat. NaHCO3-sol
  5. dry with materialand brine, dried over Na2SO4
  6. customRemoval of the solvent in vacuum
  7. waitleft the title compound as an orange oil (6.409 g, 100%)

Sources & evidence

ORD record
ord-f516a7860dc24a049534acdead280f95
Source dataset
uspto-grants-2012_04
Patent number
US08163778B2

Reaction notes

Loading…