Einecs 211-027-4 → HCID 23111405, compound
Reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N: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)=[CH:5][C:4]=1[CH3:23].[Cl-].[NH+]1C=CC=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[CH3:23][C:4]1[CH:5]=[C:6]([N:9]2[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:13][CH2:14]2)[CH:7]=[CH:8][C:3]=1[OH:2]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 210 °C
Procedure
A mixture of 1-(4-methoxy-3-methylphenyl)-4-phenethyl-piperazine (327 mg) and pyridinium chloride (731 mg) was heated to 210° C. and stirred for an hour. The reaction liquid was diluted with 1 mL of toluene, and to which saturated saline solution was added. Further adding saturated aqueous sodium hydrogencarbonate solution to render the system weakly alkaline, the product was extracted with ethyl acetate-tetrahydrofuran (1:1). The organic layer was washed with saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the remaining crude product was purified on TLC (developer, chloroform: methanol=15:1) to provide 2-methyl-4-(4-phenethylpiperazin-1-yl)phenol (141 mg).
Workup
- customThe reaction liquid
- additionto which saturated saline solution was added
- extractionthe product was extracted with ethyl acetate-tetrahydrofuran (1:1)
- washThe organic layer was washed with saturated saline solution
- dry with materialdried over anhydrous magnesium sulfate
- distillationThe solvent was distilled off
- customthe remaining crude product was purified on TLC (developer, chloroform: methanol=15:1)
Sources & evidence
- ORD record
- ord-1e88e063253f4895836a0436aca109be
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07449466B2
Reaction notes
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