Triethylamine → Ethanone, 2,2,2-trifluoro-1-[4-(2-propyn-1-ylamino)phenyl]-

HRID 1722708Notes

Reaction equation

HRID 1722708 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8](F)=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[CH2:21]([NH2:24])[C:22]#[CH:23]>C(#N)C>[F:1][C:2]([F:13])([F:12])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([NH:24][CH2:21][C:22]#[CH:23])=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 695642,2,2,4'-TetrafluoroacetophenoneHCID 239041Propargylamine

Product 1

HCID 14650032Ethanone, 2,2,2-trifluoro-1-[4-(2-propyn-1-ylamino)phenyl]-Yield 100.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 8.64 g (45 mmol) of 2,2,2-trifluoro-1-(4-fluorophenyl)ethanone (Journal of Organic Chemistry, Vol. 32, pp. 1311-1318 (1967)) and 7.53 ml (54 mmol) of triethylamine in 150 ml of acetonitrile, cooled in an ice-bath, is added 31.13 ml (0.45 mol) of 2-propynylamine. The ice-bath is removed and the solution is heated under reflux for eighteen hours. The reaction solution is cooled and concentrated to give a solid, which is partitioned between ethyl acetate and water. The ethyl acetate layer is separated, dried (magnesium sulfate), and concentrated to give 10.23 g of a red-brown oil. This is applied to a column of 250 g of flash silica gel packed in n-heptane-dichloromethane (2:1). Elution with the same solvent gives 4.05 g (39.6%) of the product as a fluffy white solid; mp 96°-98° C.

Workup

  1. customThe ice-bath is removed
  2. temperaturethe solution is heated
  3. temperatureunder reflux for eighteen hours
  4. temperatureThe reaction solution is cooled
  5. concentrationconcentrated
  6. customto give a solid, which
  7. customis partitioned between ethyl acetate and water
  8. customThe ethyl acetate layer is separated
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-fab83f3f2e2645b79369912b16623065
Source dataset
uspto-grants-1989_08
Patent number
US04857530

Reaction notes

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