Dimethylamine → HCID 86725286, compound

HRID 1403190Notes

Reaction equation

HRID 1403190 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]#[CH:12].[CH3:13][NH:14][CH3:15].C1COCC1.[I-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.CCOC(C)=O>[C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[NH:4][CH2:3][CH2:2][N:14]([CH3:15])[CH3:13])#[CH:12]

Participants

8

Reactant 5

HCID 674DimethylamineHCID 5238Sodium IodideHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 86725287HCID 86725287, compound

Product 1

HCID 86725286HCID 86725286, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

N-(2-Chloroethyl)-2-ethynylaniline (0.5 g, 2.79 mmol) in ACN (16 mL) was treated with 2M dimethylamine in THF (4.2 mL, 8.37 mmol), sodium iodide (1.25 g, 8.37 mmol), sodium carbonate (887 mg, 8.37 mmol) and heated in a sealed tube at 80° C. (oil bath temperature) for 15 h, with stirring. EtOAc was added (100 mL) and the organic phase was washed first with water (100 mL) and then with brine. Removal of the volatiles by evaporation, after drying over sodium sulfate and purification of the crude over silica gel (DCM/7N NH3 in MeOH 9/1) afforded the title compound (265 mg, 50%).

Workup

  1. washthe organic phase was washed first with water (100 mL)
  2. customRemoval of the volatiles
  3. customby evaporation
  4. dry with materialafter drying over sodium sulfate and purification of the crude over silica gel (DCM/7N NH3 in MeOH 9/1)

Sources & evidence

ORD record
ord-8e23359bc3dc412e95612bb7ea8e8249
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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