Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Glyoxal | HCID 7860 | — |
| Reactant | 3-(Trifluoromethyl)benzaldehyde | HCID 67990 | — |
| Reactant | Cyclopropylamine | HCID 69828 | — |
| Reactant | Ammonium Acetate | HCID 517165 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | HCID 67133190 | HCID 67133190 | 21% |
Reaction Steps
8.17 ml=6.62 g (113.6 mmol) of cyclopropylamine and 8.90 g (113.6 mmol) of ammonium acetate were added to a solution of 6.80 g (37.9 mmol) of 3-(trifluoromethyl)benzaldehyde in 60 ml of MeOH and the reaction mixture was cooled down to 0° C. While stirring, 9.59 ml=16.49 g (113.6 mmol) of glyoxal solution (40% in water) was added and then the reaction was warmed up to 50° C. After cooling down to RT, the solvents were evaporated and the residue dissolved in water and Et2O. The reaction mixture was extracted three times with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (CH2Cl2) to give 1.96 g (21%) of the title compound as light red oil. MS: 253.1 (MH+).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07935707B2 |
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| Source dataset | uspto-grants-2011_05 |
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| ORD ID | ord-8fc6468d21174d3fabf1415d45c5e170 |
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| Source note | uspto-grants-2011_05 |
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