Water → 4-(2-chlorophenyl)-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)piperazine-1-carboxamide
Reaction equation
[OH:1][CH:2]1[CH2:11][C:10]2[C:9]([NH:12][C:13](=[O:15])[O-])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:4][CH2:3]1.Cl.[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]1.N12CCCN=C1CCCCC2.O>O1CCCC1>[Cl:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N:24]1[CH2:29][CH2:28][N:27]([C:13]([NH:12][C:9]2[C:10]3[CH2:11][CH:2]([OH:1])[CH2:3][CH2:4][C:5]=3[CH:6]=[CH:7][CH:8]=2)=[O:15])[CH2:26][CH2:25]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a mixture of (7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)carbamate (141 mg, 0.50 mmol) and 2-chlorophenyl piperazine hydrochloride (155 mg, 0.66 mmol) in tetrahydrofuran (15 mL) was added 1,8-diazabicyclo[5.4.0]undec-7-ene (228 mg, 1.50 mmol) at room temperature, and the mixture was stirred for 30 minutes. Water was added and the mixture was extracted with ethylacetate. The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethylacetate/hexane=1/1) to provide 4-(2-chlorophenyl)-N-(7-hydroxy-5,6,7,8-tetrahydronaphthalen-1-yl)piperazine-1-carboxamide (103 mg).
Workup
- extractionthe mixture was extracted with ethylacetate
- dry with materialThe organic layer was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe obtained residue was purified by silica gel column chromatography (eluent: ethylacetate/hexane=1/1)
Sources & evidence
- ORD record
- ord-1d3dce334e2c4d06855cf6e47ef9fb7a
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07615557B2
Reaction notes
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