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

HRID 1706473Notes

Reaction equation

C(OC1C=CC(Cl)=C[C:7]=1[C:8]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=1)=[O:9])CCC.N1CCOCC1.[S]>>[C:8]([NH:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)(=[O:9])[CH3:7]

Participants

Reactant 3

HCID 8083Morpholine

HCID 5362487Sulfur

HCID 20336031HCID 20336031, compound

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

customis prepared in the following manner

Sources & evidence

ORD record: ord-6649cb2a42e74953853b024fa29cd907
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04207341

Reaction notes

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