1-(2-Chloroethyl)pyrrolidine hydrochloride → 1-[2-(4-Bromo-2-methoxyphenoxy)ethyl]pyrrolidine

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([O:9][CH3:10])[CH:3]=1.Cl.Cl[CH2:13][CH2:14][N:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:13][CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:4]([O:9][CH3:10])[CH:3]=1

Participants

Reactant 2

HCID 816681-(2-Chloroethyl)pyrrolidine hydrochloride

HCID 2622344-Bromo-2-methoxyphenol

Product 1

HCID 229943381-[2-(4-Bromo-2-methoxyphenoxy)ethyl]pyrrolidine

Procedure

The product was obtained analogously to Example 24.1a starting from 4-bromo-2-methoxyphenol and 1-(2-chloroethyl)pyrrolidine hydrochloride. Yield: 3.96 g (45% of theoretical); C13H19BrNO2 (M=300.192); calc.: molpeak (M+H)+: 300/302 (Br); found: molpeak (M+H)+: 300/302 (Br); HPLC-MS: 4.67 minutes (method A).

Workup

customThe product was obtained analogously to Example 24.1a
custom4.67 minutes (method A)

Sources & evidence

ORD record: ord-ab5c9fbf59724ae586c30cd0eb674a38
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592358B2

Reaction notes

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