Benzeneacetic acid, .alpha.-ethyl-, ethyl ester → HCID 23453027, compound

HRID 1277678Notes

Reaction equation

HRID 1277678 reaction equation
[ClH:1].NC[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:17][CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1.C1(C(CC)C(OCC)=O)C=CC=CC=1>>[Cl:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:17][CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:7][CH:6]=1

Participants

3

Reactant 2

HCID 97713Benzeneacetic acid, .alpha.-ethyl-, ethyl esterHCID 23453105HCID 23453105, compound

Product 1

HCID 23453027HCID 23453027, compound

Procedure

For the preparation of ethyl 2-[4-(2-aminoethyl)-phenyl]-butyrate hydrochloride, ethyl 2-phenylbutyrate is chloromethylated and the ethyl 2-(p-chloromethylphenyl)-butyrate obtained (b.p. 117°-123° C./0.2 mm Hg) is reacted with potassium cyanide in acetone to give ethyl 2-(p-cyanomethylphenyl)-butyrate (b.p. 156°-160° C./0.3 mm Hg). By the catalytic hydrogenation of the nitrile group in the presence of a palladium/charcoal catalyst in alcoholic hydrochloric acid solution, there is obtained ethyl 2-[4-(2-aminoethyl)-phenyl]-butyrate hydrochloride, which does not crystallize.

Sources & evidence

ORD record
ord-80b9324f7f794f9294dfbc90d7f03a0b
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

Loading…