HCID 12854202, compound → HCID 21492265, compound
Reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([O:12]CC)=[O:11])[CH:5]=[CH:6][C:7]=1[NH2:8].C(OC(=O)[CH:20]=[CH:21][C:22](=[O:30])[CH:23]=[CH:24]C(OCC)=O)C>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH3:15])[C:10]([OH:12])=[O:11])[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:24][CH2:23][C:22](=[O:30])[CH2:21][CH2:20]1Participants
Procedure
Moreover, the 4-fluoro-phenyl-acetonitrile can be reacted with 4-oxo-piperidine, to yield the 4-(4-oxo-piperidino)-phenyl-acetonitrile, which can be hydrolyzed to the free acid and the acid esterified, or the ethyl α-(3-chloro-4-aminophenyl)-propionate reacted with 4-oxo-2,5-heptadienedioic acid diethyl ester, saponifying and decarboxylating the reaction product, to yield the α-[3-chloro-4-(4-oxo-piperidino)-phenyl]-propionic acid. In corresponding esters, the carbonyl group can be reduced with one equivalent of Grignard compounds, e.g. methyl-, ethyl-, n-propyl-, phenyl- or 4-chlorophenyl-magnesium bromide, to yield, inter alia, the ethyl 4-[4-hydroxy-4-(methyl, ethyl, n-propyl, phenyl or 4-chlorophenyl)-piperidino]-phenyl acetate or α-[3-chloro-4-(4-hydroxy-4-methylpiperidino)-phenyl]-propionate. Said esters or the corresponding acids can be dehydrated wtih sulfuric or phosphoric acid, to yield, for example, the 4-(3-n-propyl-pent-2-enyleneimino)-phenylacetic acid or the α-[3-chloro-4-(3-methylpent-2-enyleneimino)-phenyl]-phenyl]-propionic acid.
Sources & evidence
- ORD record
- ord-3cac5d78ca5a4e2ebf9e6ec23de970c1
- Source dataset
- uspto-grants-1976_12
- Patent number
- US03997669
Reaction notes
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