Hydrochloric Acid → (3,5-Bis-trifluoromethyl-benzyl)-(3-o-tolyl-pyridin-4-ylmethyl)-amine

HRID 1975961Notes

Reaction equation

HRID 1975961 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:25]=1)[CH2:6][NH:7][C:8](=O)[C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21].Cl.[OH-].[Na+].C(OCC)(=O)C>O1CCCC1.CCOCC>[F:28][C:26]([F:27])([F:29])[C:24]1[CH:23]=[C:5]([CH:4]=[C:3]([C:2]([F:31])([F:30])[F:1])[CH:25]=1)[CH2:6][NH:7][CH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[CH3:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 22000068n-(3,5-Bis-trifluoromethyl-benzyl)-3-o-tolyl-isonicotinamide

Product 1

HCID 88053972(3,5-Bis-trifluoromethyl-benzyl)-(3-o-tolyl-pyridin-4-ylmethyl)-amineYield 51.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 0.26 g (0.59 mmol) N-(3,5-bis-trifluoromethyl-benzyl)-3-o-tolyl-isonicotinamide in 5 ml tetrahydrofuran 3.6 ml of a 1M solution of BH3 in tetrahydrofuran was added and the reaction mixture stirred for 16 h at 60°. After addition of 5 ml 3M HCl in ether the reaction mixture was stirred for 3 h at 60° C. The solution was cooled to room temperature and 10 ml 3N sodium hydroxide solution and 10 ml ethyl acetate were added. Stirring was continued for ½ h, the phases separated and the aqueous phase extracted twice with 15 ml ethyl acatate. The combined organic layers were washed with brine, dried (magnesium sulfate) and evaporated. Chromatography of the residue afforded 0.13 g (51%) of the title compound as a pale yellow oil.

Workup

  1. stirringwas stirred for 3 h at 60° C
  2. stirringStirring
  3. waitwas continued for ½ h
  4. customthe phases separated
  5. extractionthe aqueous phase extracted twice with 15 ml ethyl acatate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried (magnesium sulfate)
  8. customevaporated

Sources & evidence

ORD record
ord-25961c5551224f44b492c574e84f0d97
Source dataset
uspto-grants-2001_05
Patent number
US06225316B1

Reaction notes

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