Piperazine → 8-Chloro-5,11-dihydro-11-(1-piperazinyl)[1]benzothiepino[4,3-b]pyridine
Reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6](Cl)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3.[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>C1COCC1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]2[CH:6]([N:18]3[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:7]3[C:12]([CH2:13][S:14][C:4]=2[CH:3]=1)=[CH:11][CH:10]=[CH:9][N:8]=3Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A slurry of 8,11-dichloro-5,11-dihydro-[1]benzothiepino[4,3-b]pyridine (3.79 g, 13.43 mmol) in THF (25 ml) was added dropwise to piperazine (3.53 g, 157 mmol) in THF (50 ml) over 45 minutes. The mixture was stirred at room temperature for 5 hours and the reaction was then quenched with the slow addition of NaOH (200 ml, 2.5N) and extracted with CH2Cl2 (400 ml and 4×100 ml). The combined organic layers were washed with brine, dried (Na2SO4), decanted and concentrated; the crude product was purified by flash chromatography (10%acetone/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH) and obtained as a white solid (4.08 g, 91%); MS (FAB, M+H)=332; found: C, 61.73; H, .5.60; N, 12.40; C17H18ClN3S requires: C, 61.53; H, 5.47; N, 12.66.
Workup
- customthe reaction was then quenched with the slow addition of NaOH (200 ml, 2.5N)
- extractionextracted with CH2Cl2 (400 ml and 4×100 ml)
- washThe combined organic layers were washed with brine
- dry with materialdried (Na2SO4)
- customdecanted
- concentrationconcentrated
- customthe crude product was purified by flash chromatography (10%acetone/CH2Cl2 to 10%MeOH/CH2Cl2 /NH4OH)
Sources & evidence
- ORD record
- ord-bcd5fc92bfd94b62be628d35ece752a4
- Source dataset
- uspto-grants-2000_10
- Patent number
- US06130229
Reaction notes
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