Potassium Carbonate → N-[2,4-bis(trifluoromethyl)benzyl]-N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine

HRID 2251520Notes

Reaction equation

HRID 2251520 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[F:24][C:25]([F:39])([F:38])[C:26]1[CH:33]=[C:32]([C:34]([F:37])([F:36])[F:35])[CH:31]=[CH:30][C:27]=1[CH2:28]Br>O1CCOCC1>[F:24][C:25]([F:38])([F:39])[C:26]1[CH:33]=[C:32]([C:34]([F:37])([F:35])[F:36])[CH:31]=[CH:30][C:27]=1[CH2:28][N:11]([CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5188712,4-Bis(trifluoromethyl)benzyl bromideHCID 28549389N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine

Product 1

HCID 86598930N-[2,4-bis(trifluoromethyl)benzyl]-N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amineYield 44%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine (150 mg; 0.66 mmol) in 3 ml of dioxane, under nitrogen, was treated with K2CO3 (113 mg; 0.82 mmol) and 2,4-bis-trifluoromethyl-benzyl bromide (0.13 ml; 0.69 mmol) and heated in a pressure tube at 190–220C for 16 hours. Upon cooling, the reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate. The organic phase was washed with saturated brine, dried over sodium sulfate and concentrated. Purification by radial chromatography on silica gel using an ethyl acetate-hexane gradient (5–50%) afforded N-[2,4-bis(trifluoromethyl)benzyl]-N-[2-(4-methoxyphenyl)ethyl]pyridin-2-amine (130 mg; 44% yield).

Workup

  1. temperatureheated in a pressure tube at 190–220C for 16 hours
  2. temperatureUpon cooling
  3. customthe reaction mixture was partitioned between ethyl acetate and saturated sodium bicarbonate
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification by radial chromatography on silica gel using an ethyl acetate-hexane gradient (5–50%)

Sources & evidence

ORD record
ord-507e680acfc14de5baa0c243d38db227
Source dataset
uspto-grants-2008_01
Patent number
US07319104B2

Reaction notes

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