Naphthalene → 2-Phenethylpiperazine
반응식
[CH2:1]([CH:9]1[CH2:14][N:13](S(C2C=CC(C)=CC=2)(=O)=O)[CH2:12][CH2:11][N:10]1S(C1C=CC(C)=CC=1)(=O)=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C1C2C(=CC=CC=2)C=CC=1>C1COCC1>[CH2:1]([CH:9]1[CH2:14][NH:13][CH2:12][CH2:11][NH:10]1)[CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1참가 물질
4
반응 조건
- 온도
- -78 °C
실험 절차
Add 2-phenethyl-1,4-bis-(toluene-4-sulfonyl)-piperazine (100 mg, 0.2 mmol) in THF (2 mL) to a cooled (−78° C.) suspension of metallic Na (36.8 mg, 1.6 mmol) and naphthalene (230.4 mg, 1.8 mmol) in fresh distilled THF(4 mL) was under nitrogen and stir at −78° C. After 1 hour, TLC indicated the reaction is complete. Hydrolyze the reaction with brine (10 mL) and extract with CH2Cl2 (3×10 mL). Combine the organic layers and dry over Na2SO4 and evaporate. Pass the resulting residue through a SCX column to obtain the title compound as a solid: mass spectrum (electrospray): (m/z)=191.2 (M+1); 1H NMR (CDCl3): δ7.30–7.25 (m, 2H), 7.20–7.15 (m, 3H), 3.00–2.61 (m, 8H), 2.40 (t, 1H, J=11.7 Hz), 1.70 (br, 2H), 1.67–1.60 (m, 2H).