6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]-2-propenyloxy}carbostyril → N-cyclohexyl-N-(2-hydroxyethyl)-4-(6-carbostyriloxy)butyramide
Reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:5]([CH:7]=[CH:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH:15]=[CH:14]2)=[O:6]>CO.[C].[Pd]>[OH:1][CH2:2][CH2:3][N:4]([CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]1)[C:5]([CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[C:13]2[C:18](=[CH:19][CH:20]=1)[NH:17][C:16](=[O:21])[CH:15]=[CH:14]2)=[O:6]Participants
4
Procedure
1.0 Gram of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]-2-propenyloxy}carbostyril was dissolved in 50 ml of methanol and 0.1 g of 5% palladiumcarbon was added. The mixture was catalytically hydrogenated at a room temperature under an atmospheric pressure for 5 hours. After the reaction was completed, the catalyst was removed by filtration and the filtrate was concentrated by distillation under a reduced pressure to dryness. The residue thus obtained was recrystallized from chloroform-petroleum ether. 0.8 Gram of 6-{3-[N-(2-hydroxyethyl)-N-cyclohexylaminocarbonyl]propoxy}carbostyril was obtained as in the form of colorless needle-like crystals. Melting point: 165°-166° C.
Workup
- customthe catalyst was removed by filtration
- concentrationthe filtrate was concentrated by distillation under a reduced pressure to dryness
- customThe residue thus obtained
- customwas recrystallized from chloroform-petroleum ether
Sources & evidence
- ORD record
- ord-03e8e98ffea44517b5926c8622db0582
- Source dataset
- uspto-grants-1984_03
- Patent number
- US04435404
Reaction notes
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