Trifluoroacetic acid → HCID 71239589, compound

HRID 1403191Notes

Reaction equation

HRID 1403191 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O)#[CH:2].[CH3:11][N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(O)(C(F)(F)F)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH4+].[OH-]>O1CCOCC1.CCOC(C)=O>[C:1]([C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][N:15]1[CH2:16][CH2:17][N:12]([CH3:11])[CH2:13][CH2:14]1)#[CH:2]

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 14923Ammonium HydroxideHCID 531671-MethylpiperazineHCID 27716443-EthynylbenzaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 71239589HCID 71239589, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

3-Ethynylbenzaldehyde (90 mg, 0.69 mmol) and 1-methylpiperazine (92 μL, 0.828 mmol) in 1,4-dioxane (2.6 mL), under a nitrogen atmosphere, at room temperature were treated first with TFA (128 μL, 1.66 mmol), then with sodium triacetoxyborohydride (210 mg, 1.035 mmol) and stirred for 5 h. EtOAc was added to the reaction mixture (20 mL) and 10% NH4OH (15 mL) was added drop wise. The organic layer was separated, dried over sodium sulfate and evaporated. Purification of the crude by flash chromatography over silica gel (DCM/7N NH3 in MeOH 9/1) afforded the title compound (56 mg, 38%).

Workup

  1. additionwas added drop wise
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customPurification of the crude by flash chromatography over silica gel (DCM/7N NH3 in MeOH 9/1)

Sources & evidence

ORD record
ord-a7e43f372e764aad983d7ebf353b6413
Source dataset
uspto-grants-2014_12
Patent number
US08912200B2

Reaction notes

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