Dimethylamine → 2-((Dimethylamino)methyl)-4-fluorobenzonitrile

HRID 505698Notes

Reaction equation

HRID 505698 reaction equation
Br[CH2:2][C:3]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6].[CH3:12][NH:13][CH3:14]>>[CH3:12][N:13]([CH2:2][C:3]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:4]=1[C:5]#[N:6])[CH3:14]

Participants

3

Reactant 2

HCID 674DimethylamineHCID 219849902-(Bromomethyl)-4-fluorobenzonitrile

Product 1

HCID 594293842-((Dimethylamino)methyl)-4-fluorobenzonitrileYield 68%

Procedure

A mixture of 2-(bromomethyl)-4-fluorobenzonitrile (423 mg, 1.9 mmol) and 2.0 M dimethylamine (4 mL) was stirred at room temperature for thirty minutes. The mixture was then concentrated, purified by normal phase flash column chromatography, on a 20 g silica gel column (5-45% ethyl acetate/hexanes gradient), and concentrated in vacuo to yield 2-((dimethylamino)methyl)-4-fluorobenzonitrile (241 mg, 1.35 mmol, 68%). 1H NMR (400 MHz, DMSO-d6) δ ppm 7.92 (dd, J=8.59, 5.37 Hz, 1H), 7.42 (dd, J=9.94, 2.69 Hz, 1H), 7.35 (td, J=8.46, 2.69 Hz, 1H), 3.56 (s, 2H), 2.19 (s, 6H).

Workup

  1. concentrationThe mixture was then concentrated
  2. custompurified by normal phase flash column chromatography, on a 20 g silica gel column (5-45% ethyl acetate/hexanes gradient)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-244643bb5fc3449883688905ff3ffdfb
Source dataset
uspto-grants-2010_08
Patent number
US07781428B2

Reaction notes

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