Benzo(B)Thiophene → HCID 15337059, compound

HRID 1457805Notes

Reaction equation

HRID 1457805 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.C([Li])CCC.[CH2:15]([N:22]1[CH2:27][CH2:26][CH2:25][CH2:24][C:23]1=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O:29]1CCCC1>>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:25]1([OH:29])[CH2:26][CH2:27][N:22]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:23][CH2:24]1

Participants

5

Reactant 4

HCID 7221Benzo(B)ThiopheneHCID 8028TetrahydrofuranHCID 51700761-Benzyl-2-piperidoneHCID 178418339Butyllithium

Product 1

HCID 15337059HCID 15337059, compoundYield 75%

Procedure

Benzothiophene (10 g, 0.07 mol) was dissolved in tetrahydrofuran (150 ml) and cooled to -10° C. (ice/methanol). Butyl lithium (33 ml of 2.5M in hexane, 0.077 mol) was added dropwise and the reaction mixture warmed to room temperature over one hour. Following addition of N-benzyl piperidone (9.16 ml, 0.07 mol) at -40°, the reaction was stirred overnight at room temperature. The reaction mixture was concentrated in vacuo and the crude product purified by flash chromatography eluting with 20% and 30% ethyl acetate in petroleum ether to give an orange/red solid. Recrystallisation from ether afforded the title compound as a pale yellow solid (16.87g, 75%); δH (CDCl3), 1.96 (2H, m, NCH2 CH2), 1.99 (1H, s, OH), 2.25 (2H, t of d, J 13.5Hz, J 4.4Hz, NCH2CH2), 2.51 (2H, t of d, J 11.6Hz, J 2.46Hz, NCH2 CH2), 2.76 (2H, m, NCH2CH2), 3.57 (2H, s, NCH2, Ar), 7.30 (8H, m, ArH), 7.70 (1H, d, J 7Hz, ArH), 7.79 (1H, d, J 7.6Hz, ArH). m/z (ES+) 324 (M+1)+.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe crude product purified by flash chromatography
  3. washeluting with 20% and 30% ethyl acetate in petroleum ether
  4. customto give an orange/red solid
  5. customRecrystallisation from ether

Sources & evidence

ORD record
ord-54aaff304f454b1895bd4b11e1374292
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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