Malonic Acid → 3-[4-(2-Acetamidopropyl)phenyl]prop-2-enoic acid
Reaction equation
[C:1]([NH:4][CH:5]([CH3:15])[CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1)(=[O:3])[CH3:2].C(O)(=O)[CH2:17][C:18]([OH:20])=[O:19]>>[C:1]([NH:4][CH:5]([CH3:15])[CH2:6][C:7]1[CH:14]=[CH:13][C:10]([CH:11]=[CH:17][C:18]([OH:20])=[O:19])=[CH:9][CH:8]=1)(=[O:3])[CH3:2]Participants
3
Procedure
The ester hydrochloride used as starting material is prepared in the following manner: N-acetyl-4-acetylamphetamino (m.p. 99°-100° C.) is oxidized to 4-(2-acetamidopropyl)-benzoic acid (m.p. 207°-208° C.), this is reduced to give 4-(2-acetamidopropyl)-benzyl alcohol (oil) which is then oxidized to 4-(2-acetamidopropyl)-benzaldehyde (m.p. 84°-86° C.) and this is condensed with malonic acid to give 4-(2-acetamidopropyl)-cinnamic acid (m.p. 207°-208° C.) which is hydrogenated to give β-[4-(2-acetamidopropyl)-phenyl]-propionic acid (m.p. 93°-96° C.). Subsequent acid hydrolysis gives the hydrochloride of β-[4-(2-aminopropyl)-phenyl]-propionic acid which is esterified to give the above-mentioned ethyl ester hydrochloride.
Sources & evidence
- ORD record
- ord-a5e53f2e2b44471b8d2133abec7743b1
- Source dataset
- uspto-grants-1980_12
- Patent number
- US04238506
Reaction notes
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