N,N'-Dimethylethylenediamine → HCID 61709050, compound

HRID 875478Notes

Reaction equation

HRID 875478 reaction equation
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]([CH3:16])([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:10])[CH:3]=1.[N-:17]=[N+]=[N-].[Na+].CNCCNC>CS(C)=O.C(OCC)(=O)C.[Cl-].[NH4+].[Cu]I>[CH3:10][C:9]([NH:8][C:4]1[CH:3]=[C:2]([NH2:17])[CH:7]=[CH:6][N:5]=1)([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:16]

Participants

8

Reactant 3

HCID 8070N,N'-DimethylethylenediamineHCID 33557Sodium AzideHCID 71061753HCID 71061753, compound

Product 1

HCID 61709050HCID 61709050, compoundYield 34%

Reagents, catalysts & solvents 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-bromo-N-(2,4,4-trimethylpentan-2-yl)pyridin-2-amine (7.5 g, 260 mmol), sodium azide (5.07 g, 780 mmol), CuI (1.4 g, 7.8 mmol), N,N′-dimethylethane-1,2-diamine (1.3 g, 15 mmol) in dimethylsulfoxide (150 mL) was heated in a sealed reaction vessel at 90° C. for 16 hours. The reaction mixture was diluted with ethyl acetate (500 mL), saturated ammonium chloride (1000 mL) and stirred for 1 hour. The organic layer was separated and the aqueous layer was again extracted with ethyl acetate (3×300 mL). The combined organic layer was washed with brine, dried over anhydrous sodium sulphate and concentrated to give brown sticky mass which was purified by silica gel column chromatography using methanol and dichloromethane as eluent to yield 2 g (34%) of N2-(2,4,4-trimethylpentan-2-yl)pyridine-2,4-diamine.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was again extracted with ethyl acetate (3×300 mL)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. concentrationconcentrated
  6. customto give brown sticky mass which
  7. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a49fb965a3a246998f71801295d86bc5
Source dataset
uspto-grants-2015_03
Patent number
US08980911B2

Reaction notes

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