Methanol → 1-[2-Methoxy-5-(4-methoxy-naphthalene-1-sulfonyl)phenyl] piperazine
Reaction equation
F[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([S:12]([C:15]2[CH:16]=[CH:17][C:18]([O:27][CH3:28])=[C:19]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[CH:20]=2)(=[O:14])=[O:13])=[CH:4][CH:3]=1.[OH-:29].[Na+].O.[CH3:32]O>>[CH3:28][O:27][C:18]1[CH:17]=[CH:16][C:15]([S:12]([C:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:2]([O:29][CH3:32])=[CH:3][CH:4]=2)(=[O:14])=[O:13])=[CH:20][C:19]=1[N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1Participants
5
Procedure
To a solution of 1-[5-(4-fluoro-naphthalene-1-sulfonyl)2-methoxyphenyl] piperazine (0.050 g; 0.12 mmol) prepared in example 4 in methanol (2 mL) was added a solution of 6N NaOH (0.5 mL). After stirring at 80° C. for 30 min water was added (10 ml) and the mixture was extracted into ethyl acetate (20 mL). The organic phase was extracted into 2N aqueous HCl. The aqueous layer was adjusted with 6N NaOH solution to pH 14 and extracted with ethyl acetate. The organic phase was dried (Na2SO4) and concentrated in vacuo to give 1-[2-methoxy-5-(4-methoxy-naphthalene-1-sulfonyl)phenyl] piperazine (501) as a white solid (0.043 g; 88%). The hydrochloride salt was prepared from ethanol-hydrogen chloride, m. p. 240.243.0° C.
Workup
- additionwas added (10 ml)
- extractionthe mixture was extracted into ethyl acetate (20 mL)
- extractionThe organic phase was extracted into 2N aqueous HCl
- extractionextracted with ethyl acetate
- dry with materialThe organic phase was dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-9333077c6f2541afa1be6a1f3fc16a61
- Source dataset
- uspto-grants-2004_11
- Patent number
- US06825202B2
Reaction notes
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