Piperidine → HCID 66785466, compound

HRID 1095222Notes

Reaction equation

HRID 1095222 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([CH2:12][CH2:13][CH3:14])[C:9](OS(C(F)(F)F)(=O)=O)=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=N2.N1CCC[CH2:25][CH2:24]1.C[C:30]([OH:34])([C:32]#[CH:33])C.[Cl-].[NH4+:36]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:6][C:5]1[C:24]([CH3:25])=[N:36][C:8]2[C:3]([CH:4]=1)=[C:2]([F:1])[CH:11]=[C:10]([CH2:12][CH2:13][CH3:14])[C:9]=2[C:33]#[C:32][CH2:30][OH:34]

Participants

6

Reactant 4

HCID 8082PiperidineHCID 82582-Methyl-3-butyn-2-olHCID 25517Ammonium ChlorideHCID 86629165HCID 86629165, compound

Product 1

HCID 66785466HCID 66785466, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A 25 mL Schlenk tube was replaced with Ar and 5-fluoro-7-propyl-8-trifluoromethanesulfonyloxyquinoline (1.00 g, 2.97 mmol), tetrakis(triphenylphosphine)palladium (171.3 mg, 0.148 mmol), 3.55 mL of piperidine and 2-methyl-3-butyn-2-ol (381 mg, 98 mass % article, 3.75 mmol) were added thereto and the mixture was stirred at 80° C. for 3 hours. The reaction mixture was cooled to room temperature, and then a saturated aqueous ammonium chloride solution was added thereto and the mixture was extracted with diethyl ether. The extract was dried over magnesium sulfate and the solvent was distilled off under reduced pressure by an evaporator. The crude reaction product was purified by column chromatography (Hexane/AcOEt=100/0→1/5) using silica gel to give 390 mg of dimethylhydroxymethyl-5-fluoro-7-propyl-8-quinolylacetylene as a yellowish brown solid (yield: 48.4%).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was cooled to room temperature
  3. extractionthe mixture was extracted with diethyl ether
  4. dry with materialThe extract was dried over magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure by an evaporator
  6. customThe crude reaction product
  7. customwas purified by column chromatography (Hexane/AcOEt=100/0→1/5)

Sources & evidence

ORD record
ord-cfb24f578b944c3a8c68dbd6f083ddbb
Source dataset
uspto-grants-2012_03
Patent number
US08137821B2

Reaction notes

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