Naphthalene → 2-Phenethylpiperazine
Reaction equation
[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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
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).
Workup
- temperaturea cooled
- distillationin fresh distilled THF(4 mL)
- customHydrolyze the reaction with brine (10 mL)
- extractionextract with CH2Cl2 (3×10 mL)
- dry with materialCombine the organic layers and dry over Na2SO4
- customevaporate
Sources & evidence
- ORD record
- ord-8b84957afb344b8790a23036041ff02e
- Source dataset
- uspto-grants-2007_05
- Patent number
- US07214673B2
Reaction notes
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