4-[2-(acetylamino)propyl]benzoic acid → N-{1-[4-(Hydroxymethyl)phenyl]propan-2-yl}acetamide
Reaction equation
[C:1]([NH:4][CH:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:16])C)=[CH:10][CH:9]=1)[CH3:6])(=[O:3])[CH3:2].C(NC(C)CC1C=CC(C(O)=O)=CC=1)(=O)C>>[C:1]([NH:4][CH:5]([CH3:6])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][OH:16])=[CH:12][CH:13]=1)(=[O:3])[CH3:2]Participants
3
Procedure
The ester hydrochloride used as starting material is prepared in the following manner: N-acetyl-4-acetylamphetamine (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.
Workup
- customis prepared in the following manner
Sources & evidence
- ORD record
- ord-50ec0b9238d64cdf9b8ee2791c25e0bd
- Source dataset
- uspto-grants-1978_09
- Patent number
- US04113871
Reaction notes
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