Bis(2-Methoxyethyl)amine → HCID 22064352, compound

HRID 1827871Notes

Reaction equation

HRID 1827871 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](F)=[C:4]([N+:9]([O-])=O)[CH:3]=1.[CH3:12][O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][O:19][CH3:20].[H][H]>C(#N)C.[Ni]>[NH2:9][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[N:16]([CH2:17][CH2:18][O:19][CH3:20])[CH2:15][CH2:14][O:13][CH3:12]

Participants

6

Reactant 3

HCID 2383Bis(2-Methoxyethyl)amineHCID 27363284-Bromo-1-fluoro-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22064352HCID 22064352, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-bromo-1-fluoro-2-nitrobenzene (0.44 g, 2mmol) 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), and treated with Raney nickel (50% water suspension, 0.40 g, 6.8 mmol). The vial was filled with excessive hydrogen, shaken at 50° C. for 1 hour, filtered, and concentrated. The concentrate was purified by preparative HPLC with acetonitrile/water containing 0.1% TFA to provide the desired product. MS (APCI(+)) m/z 304 (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. concentrationconcentrated
  6. customThe concentrate was purified by preparative HPLC with acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-16940515ae8d4bf8b333aebe0fd5cf1b
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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