Water → 2,4,6-Trimethyl-N-[[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl](phenyl)methyl]aniline

HRID 1944825Notes

Reaction equation

HRID 1944825 reaction equation
[C:1]1([CH3:36])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[N:9]=[CH:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]=2[CH2:27][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[N:12]=1.C1COCC1.[Li][C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1.O>CCOCC>[CH3:36][C:1]1[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=[CH:19][C:18]=2[CH2:27][NH:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[N:12]=1)[C:43]1[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 8028TetrahydrofuranHCID 66795918Mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amineHCID 178506676HCID 178506676, compound

Product 1

HCID 667957072,4,6-Trimethyl-N-[[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl](phenyl)methyl]aniline

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 1.05 g (2.23 mmol) of mesityl{[6-(2-{[(2-methylphenyl)amino]methyl}-1-naphthyl)pyridin-2-yl]methylene}amine in 20 ml of THF 7.60 ml (5.60 mmol) of 0.74 M PhLi in ether was added by vigorous stirring at −78° C. The resulting mixture was heated to room temperature and then stirred for 10 min. Further on, 2 ml of water was added, and then the reaction mixture was poured into 50 ml of water. The crude product was extracted with 3×20 ml of ether. The organic extract was washed by 2×30 ml of water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.). Yield 0.90 g (66%) of yellow oil. Anal. calc. for C39H37N3: C, 85.52; H, 6.81; N, 7.67. Found: C, 85.73; H, 6.98; N, 7.54. For 1H NMR (in CDCl3) see FIG. 2—Bottom spectrum.

Workup

  1. temperatureThe resulting mixture was heated to room temperature
  2. stirringstirred for 10 min
  3. extractionThe crude product was extracted with 3×20 ml of ether
  4. extractionThe organic extract
  5. washwas washed by 2×30 ml of water
  6. dry with materialdried over K2CO3
  7. customevaporated to dryness
  8. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: hexanes-ethyl acetate=5:1, vol.)

Sources & evidence

ORD record
ord-afedf8f848be46a89d8365824fe7e2f4
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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