Diisopropylamine → HCID 9907318, compound

HRID 49958Notes

Reaction equation

HRID 49958 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([N:7]([CH3:11])[C:8](=[O:10])[CH3:9])=[CH:5][CH:4]=1.C([N-]C(C)C)(C)C.[Li+].C(NC(C)C)(C)C.C([Li])CCC.[CH2:34]([N:41]1[CH2:46][CH2:45][C:44](=[O:47])[CH2:43][CH2:42]1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O.O1CCCC1>[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]([N:7]([CH3:11])[C:8](=[O:10])[CH2:9][C:44]2([OH:47])[CH2:45][CH2:46][N:41]([CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[CH2:42][CH2:43]2)=[CH:5][CH:4]=1

Participants

8

Reactant 5

HCID 7912DiisopropylamineHCID 192201-Benzyl-4-piperidoneHCID 142032Acetamide, N-(4-methoxyphenyl)-N-methyl-HCID 2724682Lithium diisopropylamideHCID 178418339Butyllithium

Product 1

HCID 9907318HCID 9907318, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

A solution of 4′-methoxy-N-methylacetanilide (12 g) in an anhydrous tetrahydrofuran (30 mL) was added to a solution in an anhydrous tetrahydrofuran (100 mL) of lithium diisopropylamide prepared from diisopropylamine (10.5 mL) and n-butyl lithium (1.53M hexane solution; 48 mL) at below −65° C., and the mixture was stirred at −78° C. for 15 minutes. An anhydrous tetrahydrofuran solution (20 mL) of 1-benzylpiperidin-4-one (12.7 g) was then added to this reaction mixture at below −65° C., and the resulting mixture was stirred at −78° C. for 10 minutes. After increasing the temperature to room temperature, water was added to the mixture, and the mixed solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous sodium sulfate, followed by distilling off the solvent under reduced pressure. The residue obtained was recrystallized from ether-hexane to obtain the titled compound (17.2 g).

Workup

  1. stirringthe resulting mixture was stirred at −78° C. for 10 minutes
  2. temperatureAfter increasing the temperature to room temperature
  3. extractionthe mixed solution was extracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationby distilling off the solvent under reduced pressure
  7. customThe residue obtained
  8. customwas recrystallized from ether-hexane

Sources & evidence

ORD record
ord-7da2c7e3439d4fd09da343e794317901
Source dataset
uspto-grants-2004_03
Patent number
US06710060B2

Reaction notes

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