HCID 15681286, compound → HCID 18930330, compound

HRID 266100Notes

Reaction equation

HRID 266100 reaction equation
[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][C:18]1[S:19][CH:20]=[CH:21][CH:22]=1>O1CCCC1>[C:1]1([CH2:7][CH2:8][N:9]2[CH2:14][CH2:13][CH:12]([CH:15]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[OH:16])[CH2:11][CH2:10]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15681286HCID 15681286, compoundHCID 178418439HCID 178418439, compound

Product 1

HCID 18930330HCID 18930330, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve 1-(2-phenylethyl)-4-piperidinecarboxaldehyde (10.0 g, 46.02 mmol) in anhydrous tetrahydrofuran (300 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, a solution of 2-lithiothiophene (46.02 mL of a 1M solution in tetrahydrofuran, 46.02 mmol) and stir for 3 hours at -78° C. Quench with saturated ammonium chloride, separate the organic phase and extract the aqueous phase with ethyl acetate. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (ethyl acetate) and recrystallize (cyclohexane) to give the title compound as a white solid; mp 123°-125° C.

Workup

  1. additionAdd, by dropwise addition
  2. customQuench with saturated ammonium chloride
  3. customseparate the organic phase
  4. extractionextract the aqueous phase with ethyl acetate
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by chromatography (ethyl acetate)
  8. customrecrystallize (cyclohexane)

Sources & evidence

ORD record
ord-678f947c4521420ea5d0fc69a260f5cc
Source dataset
uspto-grants-1997_07
Patent number
US05650416

Reaction notes

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