HCID 10379653, compound → HCID 18930354, compound

HRID 1491701Notes

Reaction equation

HRID 1491701 reaction equation
[C:1]1([C:7]([CH:9]2[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:11][CH2:10]2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li][C:24]1[S:25][CH:26]=[CH:27][CH:28]=1>O1CCCC1>[C:17]1([CH2:16][CH2:15][N:12]2[CH2:13][CH2:14][CH:9]([C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:24]3[S:25][CH:26]=[CH:27][CH:28]=3)[OH:8])[CH2:10][CH2:11]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 10379653HCID 10379653, compoundHCID 178418439HCID 178418439, compound

Product 1

HCID 18930354HCID 18930354, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dissolve phenyl[1-(2-phenylethyl)-4-piperidinyl]methanone (4.45 g, 15.16 mmol) in anhydrous tetrahydrofuran (40 mL), place under an argon atmosphere and cool to -78° C. Add, by dropwise addition, 2-lithiothiophene (15.16 mL of a 1M solution in tetrahydrofuran, 15.16 mmol) and stir at -78° C. for 1.5 hours. Quench with saturated ammonium chloride, separate the organic phase and extract the aqueous phase with ethyl ether. Combine the organic phases, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (50% ethyl acetate/hexane) and recrystallize (cyclohexane) to give the title compound as a white crystalline solid; mp 143°-144° C.

Workup

  1. customQuench with saturated ammonium chloride
  2. customseparate the organic phase
  3. extractionextract the aqueous phase with ethyl ether
  4. dry with materialdry (MgSO4)
  5. customevaporate the solvent in vacuo
  6. customPurify by chromatography (50% ethyl acetate/hexane)
  7. customrecrystallize (cyclohexane)

Sources & evidence

ORD record
ord-f9abe9e4e0b84131ac2ee9b36038ae0f
Source dataset
uspto-grants-1994_12
Patent number
US05371093

Reaction notes

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