Bis(2-Methoxyethyl)amine → HCID 22064351, compound

HRID 1827872Notes

Reaction equation

HRID 1827872 reaction equation
[Cl: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]([Cl: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 676604-Chloro-1-fluoro-2-nitrobenzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 22064351HCID 22064351, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-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 concentrate and the concentrate was purified by HPLC with acetonitrile/water containing 0.1% TFA to provide the desired product. MS (APCI(+)) m/z 260 (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 concentrate
  6. customthe concentrate was purified by HPLC with acetonitrile/water containing 0.1% TFA

Sources & evidence

ORD record
ord-8066baf335634ce5a78fb4d82d911a39
Source dataset
uspto-grants-2006_06
Patent number
US07056925B2

Reaction notes

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