Tetrahydrofuran → 1-Benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile

HRID 975113Notes

Reaction equation

HRID 975113 reaction equation
O1CCCC1.[C:6]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[C:20]#[N:21])(=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:22](I)[CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O>[C:6]([N:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1([CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:20]#[N:21])(=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 28503Benzene, (2-iodoethyl)-HCID 190288951-Benzoyl-2-piperidinecarbonitrile

Product 1

HCID 190288501-Benzoyl-2-(2-phenylethyl)-2-piperidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To 200 ml of tetrahydrofuran containing 140 mmol lithium diisopropylamide was added 15 g of solid 1-benzoyl-2-piperidinecarbonitrile at -78° C. The mixture was stirred for 30 minutes, after which 100 ml of tetrahydrofuran containing 33.2 g of phenethyl iodide was added dropwise at -78° C. After completion of dropwise addition, the temperature of the reaction mixture was gradually increased to 0° C. Then, water was added and the organic layer was separated. The aqueous layer was further extracted with ethyl acetate. The pooled organic layer was dried over anhydrous magnesium sulfate and filtered and the solvent was then distilled off. The residue was purified by silica gel column chromatography using ethyl acetate-hexane (1:2) as the eluent. The solution containing the desired compound was distilled under reduced pressure and the resulting solid was recrystallized from ethyl acetate-hexane to provide 17.3 g of colorless crystals.

Workup

  1. additionAfter completion of dropwise addition
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was further extracted with ethyl acetate
  4. dry with materialThe pooled organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. distillationthe solvent was then distilled off
  7. customThe residue was purified by silica gel column chromatography
  8. additionThe solution containing the desired compound
  9. distillationwas distilled under reduced pressure
  10. customthe resulting solid was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-0bfec3304083477fa3deee35b488402d
Source dataset
uspto-grants-1997_03
Patent number
US05607939

Reaction notes

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