Dimethylformamide → Aniline, p-isopropyl-N-methyl-

HRID 63665Notes

Reaction equation

HRID 63665 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.CN.CC([O-])=O.[K+].[CH3:18][N:19](C=O)C>O.[Cu]I>[CH3:18][NH:19][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6329MethylamineHCID 114621-Bromo-4-isopropylbenzeneHCID 517044Potassium Acetate

Product 1

HCID 138880Aniline, p-isopropyl-N-methyl-Yield 34%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-bromo-4-isopropylbenzene (1.0 g, 5.03 mmol), methylamine (25 mL, 50.0 mmol), CuI (1.15 g, 6.0 mmol), KOAc (1.24 g, 12.6 mmol) and DMF (30 mL) in a sealed tube under N2 was heated to 100° C. overnight. The mixture was cooled to r.t., diluted with water (100 mL), and extracted with EtOAc. The organic layer was dried (Na2SO4), concentrated, and purified by silica gel chromatography (PE:EtOAc=10:1) to give 254 mg (34%) of the title compound as a yellow oil. [M+H] Calc'd for C10H15N, 150. Found, 150.

Workup

  1. temperatureThe mixture was cooled to r.t.
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography (PE:EtOAc=10:1)

Sources & evidence

ORD record
ord-b827368ada3f471fb78eca7af238f02c
Source dataset
uspto-grants-2016_09
Patent number
US09447046B2

Reaction notes

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