Hydrochloric Acid → HCID 178473072, compound
Reaction equation
CN(C)[C:3](=[CH:9][CH:10]=[C:11]([S:26][CH3:27])[C:12](=[O:25])[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5].Cl.C([OH:32])C>>[OH:32][C:3](=[CH:9][CH:10]=[C:11]([S:26][CH3:27])[C:12](=[O:25])[C:13]1[CH:18]=[CH:17][C:16]([N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:15][CH:14]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
Conditions
- Temperature
- 20 °C
Procedure
The procedure is as in Example 4, starting with ethyl 2-dimethylamino-5-methylthio-6-oxo-6-(4-piperidinophenyl)-2,4-hexadienoate (23.5 g) and 1N hydrochloric acid (139 cc) in ethanol (139 cc). The mixture is stirred for 16 hours at a temperature in the region of 20° C. After purification by chromatography on a silica column with dichloromethane as eluent and a second chromatography on a second silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluents; the corresponding eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa). The residue is recrystallized in boiling isopropyl ether (100 cc). Ethyl 2-hydroxy-5-methylthio-6-oxo-6-(4-piperidinophenyl)-2,4-hexadienoate (3 g), m.p. 65° C., is thereby obtained.
Workup
- customAfter purification by chromatography on a silica column with dichloromethane as eluent
- additiona second chromatography on a second silica column with a mixture of cyclohexane and ethyl acetate (50:50 by volume) as eluents
- concentrationthe corresponding eluate is concentrated to dryness at 40° C. under reduced pressure (20 mm Hg; 2.7 kPa)
- customThe residue is recrystallized
Sources & evidence
- ORD record
- ord-33bad7a63dfd466489e8f021ea7033dc
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04971979
Reaction notes
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