1,2,3,4-Tetrahydroisoquinoline → 2-[2-(2-Methoxy-4-nitrophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline

HRID 735142Notes

Reaction equation

HRID 735142 reaction equation
Br[CH2:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=1[O:14][CH3:15].[CH2:16]1[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[CH2:19][CH2:18][NH:17]1>ClCCl.CO>[CH3:15][O:14][C:6]1[CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=[CH:10][C:5]=1[O:4][CH2:3][CH2:2][N:17]1[CH2:18][CH2:19][C:20]2[C:25](=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:16]1

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 129372541-(2-Bromoethoxy)2-methoxy-4-nitrobenzene

Product 1

HCID 688163292-[2-(2-Methoxy-4-nitrophenoxy)ethyl]-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Prepared analogously to Example 1.1.c. from 1 g (3.622 mmol) of 1-(2-bromoethoxy)-2-methoxy-4-nitrobenzene and 1.36 mL (10.87 mmol) of 1,2,3,4-tetrahydroisoquinoline. Yield: 1.4 g (77% of theory); C18H20N2O4 (M=328.36); calc.: molecular ion peak (M+H)+: 329; found: molecular ion peak (M+H)+: 329; Rf value: 0.7 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 1.1.c

Sources & evidence

ORD record
ord-d60826dd6dd3487bb9a6cf8b186fbba5
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

Loading…