Hydrochloric Acid → HCID 67532282, compound

HRID 2358037Notes

Reaction equation

HRID 2358037 reaction equation
[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10](F)=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH2:5][CH2:4]1)[CH3:2].C([OH:22])C#CC.CC(C)([O-])C.[K+].Cl>CS(C)=O>[CH2:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[C:10]([OH:22])=[C:11]([CH:14]=[CH:15][CH:16]=2)[C:12]#[N:13])[CH2:5][CH2:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 129912-Butyn-1-olHCID 11715598HCID 11715598, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67532282HCID 67532282, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of 3-(1-ethylpiperidin-4-yl)-2-fluorobenzonitrile (10 mg, 0.031 mmol) in dimethylsulfoxide (1 ml) was added 2-butyn-1-ol (4.3 mg, 0.062 mmol) and potassium-tert-butoxide (7 mg, 0.063 mmol). The mixture was heated to 125° C. in a sealed tube under microwave radiation for 120 s. Aqueous hydrochloric acid (10%, 10 ml) was added and the aqueous phase was washed with diethyl ether (2×20 ml). The aqueous phase was basified by addition of sodium hydroxide (5 M, 5 ml) and extracted with ethyl acetate (3×20 ml). The combined organic phase was dried (MgSO4) and evaporated under reduced pressure to give the title compound. MS m/z (relative intensity, 70 eV) 230 (M+, 60), 229 (24), 216 (23), 215 (bp) 110 (30).

Workup

  1. washthe aqueous phase was washed with diethyl ether (2×20 ml)
  2. additionThe aqueous phase was basified by addition of sodium hydroxide (5 M, 5 ml)
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. dry with materialThe combined organic phase was dried (MgSO4)
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-488c1daa4bc74bcca6c2eaab1d1cfacf
Source dataset
uspto-grants-2010_07
Patent number
US07763639B2

Reaction notes

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