Morpholine → 2-[4-(2-Acetamidoethyl)phenyl]acetic acid

HRID 1277663Notes

Reaction equation

HRID 1277663 reaction equation
Cl.[NH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([O:14]CC)=[O:13])=[CH:7][CH:6]=1.N1CC[O:20][CH2:19][CH2:18]1.[S]>>[C:19]([NH:2][CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH2:11][C:12]([OH:14])=[O:13])=[CH:9][CH:10]=1)(=[O:20])[CH3:18]

Participants

4

Reactant 3

HCID 8083MorpholineHCID 5362487SulfurHCID 20463408Ethyl 4-(2-aminoethyl)-phenylacetate hydrochloride

Product 1

HCID 234530992-[4-(2-Acetamidoethyl)phenyl]acetic acid

Procedure

The ethyl 4-(2-aminoethyl)-phenylacetate hydrochloride used as starting material is prepared in the following manner: 4-(2-acetamidoethyl)-acetophenone is reacted with morpholine and sulfur to give the thiomorpholide of 4-(2-acetamidoethyl)-phenylacetic acid (m.p. 117°-118° C.). Subsequent alkaline saponification, followed by esterification with ethanolic hydrochloric acid, gives ethyl 4-(2-aminoethyl)-phenylacetate hydrochloride; m.p. 177°-178° C., after recrystallization from ethanol.

Workup

  1. customis prepared in the following manner

Sources & evidence

ORD record
ord-423fcfdea0c94f6d938cd28e8597975d
Source dataset
uspto-grants-1981_07
Patent number
US04278680

Reaction notes

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