Propargyl bromide → 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid
Reaction equation
O.Cl.[N:3]1([C:9]2[C:20]3=[C:21]4[N:16]([CH:17]([CH3:22])[CH2:18][CH2:19]3)[CH:15]=[C:14]([C:23]([OH:25])=[O:24])[C:13](=[O:26])[C:12]4=[CH:11][C:10]=2[Cl:27])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[CH2:28](Br)[C:29]#[CH:30].C(N(CC)CC)C>CN(C)C=O>[CH2:30]([N:6]1[CH2:7][CH2:8][N:3]([C:9]2[C:20]3=[C:21]4[N:16]([CH:17]([CH3:22])[CH2:18][CH2:19]3)[CH:15]=[C:14]([C:23]([OH:25])=[O:24])[C:13](=[O:26])[C:12]4=[CH:11][C:10]=2[Cl:27])[CH2:4][CH2:5]1)[C:29]#[CH:28]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 90 °C
Procedure
A mixture of 0.8 g of 8-(1-piperazinyl)-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]-quinolizine 2-carboxylic acid hydrochloride hydrate, 0.4 ml of propargyl bromide, 0.8 ml of triethylamine and 10 ml of dimethylformamide was allowed to react by heating at 90° C. for 5 hours. After completion of the reaction insoluble substances were removed by filtration. After concentration under reduced pressure the filtrate was purified through a silica gel column chromatography (silica gel: Wako C-200, a trade name for a product of Wako Junyaku Co., Ltd.; eluent: chloroform-methanol (8:1 by volume)) to obtain 0.3 g of 8-[4-(2-propynyl)-1-piperazinyl]-9-chloro-5-methyl-6,7-dihydro-1-oxo-1H,5H-benzo[ij]quinolizine-2-carboxylic acid as pale yellow rhombic crystals having a melting point of 211° to 213° C.
Workup
- customto react
- customAfter completion of the reaction insoluble substances were removed by filtration
- concentrationAfter concentration under reduced pressure the filtrate
- customwas purified through a silica gel column chromatography (silica gel
Sources & evidence
- ORD record
- ord-6994b5d2f8f84c6693370753eeadcace
- Source dataset
- uspto-grants-1983_11
- Patent number
- US04416884
Reaction notes
Loading…