Dibenzylamine → N,N-dibenzyl-6-chloro-5-(trifluoromethyl)pyridin-2-amine

HRID 1805151Notes

Reaction equation

HRID 1805151 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4](Cl)[N:3]=1.[CH2:13]([NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C.CN1CCCC1=O>>[CH2:21]([N:20]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:4]1[CH:5]=[CH:6][C:7]([C:8]([F:11])([F:10])[F:9])=[C:2]([Cl:1])[N:3]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 7656DibenzylamineHCID 8471TriethylamineHCID 13387N-methyl-2-pyrrolidoneHCID 18103372,6-Dichloro-3-(trifluoromethyl)pyridine

Product 1

HCID 11810923N,N-dibenzyl-6-chloro-5-(trifluoromethyl)pyridin-2-amineYield 86%

Conditions

Temperature
120 °C

Procedure

A mixture of 2,6-dichloro-3-(trifluoromethyl)pyridine (1.0 g, 4.63 mmol), dibenzylamine (913 mg, 890 μL, 4.63 mmol), triethylamine (1.2 mL, 8.61 mmol) and 1-methyl-2-pyrrolidone (6 mL, 62.22 mmol) was heated at 120° C. for 9 h. The reaction mixture was cooled to the room temperature and poured into ice-water, extracted with EtOAc (20 mL×3), the combined organic layers were dried over anhydrous Na2SO4, filtered, concentrated and purified by silca gel column chromatography (2%-10% EtOAc in petroleum ether as eluant) to give N,N-dibenzyl-6-chloro-5-(trifluoromethyl)pyridin-2-amine (1.5 g, 86%) as an oil. 1H NMR (300 MHz, CDCl3) δ 7.59 (d, J=8.7 Hz, 1H), 7.37-7.21 (m, 10H), 6.32 (d, J=8.7 Hz, 1H), 4.80 (s, 4H).

Workup

  1. temperatureThe reaction mixture was cooled to the room temperature
  2. extractionextracted with EtOAc (20 mL×3)
  3. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silca gel column chromatography (2%-10% EtOAc in petroleum ether as eluant)

Sources & evidence

ORD record
ord-ba5273b8c0c54d22905b733c630fc82e
Source dataset
uspto-grants-2013_01
Patent number
US08354427B2

Reaction notes

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