Bis(2-Methoxyethyl)amine → HCID 22064354, compound

HRID 1827873Notes

Reaction equation

HRID 1827873 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6](F)=[C:5]([N+:10]([O-])=O)[CH:4]=1)#[N:2].[CH3:13][O:14][CH2:15][CH2:16][NH:17][CH2:18][CH2:19][O:20][CH3:21].[H][H]>C(#N)C.[Ni]>[NH2:10][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][C:6]=1[N:17]([CH2:18][CH2:19][O:20][CH3:21])[CH2:16][CH2:15][O:14][CH3:13])[C:1]#[N:2]

Participants

6

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 27746544-Fluoro-3-nitrobenzonitrileHCID 178418361HCID 178418361, compound

Product 1

HCID 22064354HCID 22064354, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-cyano-1-fluoro-2-nitrobenzene (35.1 mg, 0.2 mmol) and N,N-bis(2-methoxyethyl)amine (0.266 g, 2.4 mmol) in acetonitrile (10 mL) in a capped 20-mL vial was shaken at 80° C. overnight and concentrated. The concentrate was dissolved in methanol (10 mL), treated with Raney nickel (50% water suspension, 0.40 g, 6.8 mmol), filled with excess hydrogen, shaken at 50° C. for 1 hour, and filtered. The filtrate was concentrated and the concentrate was purified by HPLC with acetonitrile/water containing 0.1% TFA to give the desired compound. MS (APCI(+)) m/z 250 (M+H)+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in methanol (10 mL)
  3. stirringshaken at 50° C. for 1 hour
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe concentrate was purified by HPLC with acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-607fe14b7ebd4fb081fb5414e18c6d83
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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