Formaldehyde → HCID 86712754, compound

HRID 1754546Notes

Reaction equation

HRID 1754546 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]([CH2:18][CH2:19][NH2:20])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C=O.F[C:24](F)(F)C(O)=O>C(O)C>[CH2:1]([N:8]1[CH:24]=[C:13]2[CH:14]=[CH:15][CH2:16][C:17]3[NH:20][CH2:19][CH2:18][N:11]([C:12]=32)[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 86712755HCID 86712755, compound

Product 1

HCID 86712754HCID 86712754, compoundYield 39.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1.089 g (4.07 mmol) of 2-(4-benzyl-3,4-dihydro-2H-quinoxalin-1-yl)ethylamine and 20 ml ethanol was treated with 122 mg (4.07 mmol) of formaldehyde and 511 mg (4.48 mmol) of trifluoroacetic acid and stirred over night at room temperature. The solvent was evaporated and dichloromethane was added to the crude mixture. The organic phase was washed with 1 molar sodium hydroxide solution. The organic phase was dried and purified by column chromatography on silica (eluent: starting with dichloromethane and then up to 100% methanol) to yield 448 mg of the title compound.

Workup

  1. customThe solvent was evaporated
  2. additiondichloromethane was added to the crude mixture
  3. washThe organic phase was washed with 1 molar sodium hydroxide solution
  4. customThe organic phase was dried
  5. custompurified by column chromatography on silica (eluent

Sources & evidence

ORD record
ord-dbbc037ddbc34c8390547d6a8d783eab
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

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