Benzylamine → HCID 84142040, compound

HRID 1504782Notes

Reaction equation

HRID 1504782 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.C(N(CC)C(C)C)(C)C.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN1C(=O)CCC1.O>[CH2:19]([NH:26][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([Cl:9])[N:3]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 7504BenzylamineHCID 81531DiisopropylethylamineHCID 108989972,6-Dichloro-4-methylpyridine

Product 1

HCID 84142040HCID 84142040, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
150 °C

Procedure

2,6-Dichloro-4-methylpyridine (2.00 g, 12.3 mmol) was suspended in NMP (10 mL). N,N-Diisopropylethylamine (4.31 mL, 24.7 mmol) and benzylamine (1.42 mL, 13.0 mmol) were added, and the reaction mixture was heated to 150° C. in a microwave for 90 minutes. The reaction mixture was allowed to cool to room temperature, diluted with water, and extracted with diethyl ether (2×). The combined organics were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified via silica gel column chromatography (0-10% ethyl acetate/hexanes, linear gradient) to give N-benzyl-6-chloro-4-methylpyridin-2-amine. MS ESI calc'd. for C13H14ClN2 [M+H]+ 233. found 233.

Workup

  1. temperatureto cool to room temperature
  2. extractionextracted with diethyl ether (2×)
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified via silica gel column chromatography (0-10% ethyl acetate/hexanes, linear gradient)

Sources & evidence

ORD record
ord-7d99c45320764d2988ac0aa64e5a4a8c
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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