Hydrochloric Acid → HCID 54403381, compound

HRID 376832Notes

Reaction equation

HRID 376832 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[O:4][N:3]=1.C([Li])CCC.[CH3:13][N:14]1[CH2:19][CH2:18][CH2:17][C:16](=[O:20])[CH2:15]1.Cl>O1CCCC1.O>[OH:20][C:16]1([CH2:7][C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)[CH2:17][CH2:18][CH2:19][N:14]([CH3:13])[CH2:15]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 93123,5-DimethylisoxazoleHCID 796563-Piperidinone, 1-methyl-HCID 178418339Butyllithium

Product 1

HCID 54403381HCID 54403381, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,5-dimethylisoxazol (4.86 g, 50 mmol) in dry tetrahydrofuran (15 ml) cooled to -78° C was added butyllithium (2.5 M in hexane, 50 mmol). The reaction mixture was stirred for 0.5 h. 1-methyl-piperidin-3-one (2.70 g, 23.9 mmol) dissolved in tetrahydrofuran (25 ml) was added. The reaction mixture was stirred for another 2 h at -78° C. Water (50 ml) was added and the reaction mixture was acidified with concentrated hydrochloric acid. The water phase was extracted with ether (2×50 ml), then made alkaline with potassium carbonate and extracted with methylene chloride (4×50 ml). The combined methylene chloride phases were dried over magnesium sulphate and evaporated giving the title compound in 4.18 g (83%) yield.

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for another 2 h at -78° C
  3. extractionThe water phase was extracted with ether (2×50 ml)
  4. extractionextracted with methylene chloride (4×50 ml)
  5. dry with materialThe combined methylene chloride phases were dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-9f994661d30748f18613c68794deea6d
Source dataset
uspto-grants-2000_02
Patent number
US06022868

Reaction notes

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