HCID 14931320, compound → HCID 14931321, compound

HRID 974003Notes

Reaction equation

HRID 974003 reaction equation
[CH2:1]([N:3]([CH2:31][CH3:32])[CH2:4][C:5]#[C:6][CH2:7][NH:8][C:9](=[O:30])[C:10]([NH:23]C(=O)C(F)(F)F)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]>CC(C)=O.Cl>[CH2:31]([N:3]([CH2:1][CH3:2])[CH2:4][C:5]#[C:6][CH2:7][NH:8][C:9](=[O:30])[C:10]([NH2:23])([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[CH3:32]

Participants

4

Reactant 1

HCID 14931320HCID 14931320, compound

Product 1

HCID 14931321HCID 14931321, compoundYield 57.9%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

A mixture of N-(4-diethylamino-2-butynyl)-2-(2,2,2-trifluoroacetylamino)-2,2-diphenylacetamide (0.11 g) in acetone (2 ml) and 6N hydrochloric acid (1.0 ml) was refluxed for 24 hours. After being cooled, the solvent was evaporated in vacuo. The resulting solution was adjusted to pH 12 with aqueous solution of sodium hydroxide and the separated oil was extracted with ethyl acetate. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent to give N-(4-diethylamino-2-butynyl)-2-amino-2,2-diphenylacetamide (0.05 g).

Workup

  1. temperaturewas refluxed for 24 hours
  2. temperatureAfter being cooled
  3. customthe solvent was evaporated in vacuo
  4. extractionthe separated oil was extracted with ethyl acetate
  5. washThe extract was washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on silica gel with a mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-533771013c1d4f04b7bc9e265a92695d
Source dataset
uspto-grants-1991_11
Patent number
US05066680

Reaction notes

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