Cyclopropanemethanamine → Cyclopropylmethyl-[2-(2-methoxy-4-nitrophenoxy)ethyl]methylamine

HRID 735151Notes

Reaction equation

HRID 735151 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].[CH:16]1([CH2:19][NH2:20])[CH2:18][CH2:17]1.Cl[CH2:22]Cl.CO>>[CH:16]1([CH2:19][N:20]([CH2:2][CH2:3][O:4][C:5]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:6]=2[O:14][CH3:15])[CH3:22])[CH2:18][CH2:17]1

Participants

4

Reactant 3

HCID 75646CyclopropanemethanamineHCID 129372541-(2-Bromoethoxy)2-methoxy-4-nitrobenzeneHCID 21226129Dichloromethane methanol

Product 1

HCID 68816696Cyclopropylmethyl-[2-(2-methoxy-4-nitrophenoxy)ethyl]methylamine

Procedure

Prepared analogously to Example 1.1.c. from 1 g (3.62 mmol) of 1-(2-bromoethoxy)-2-methoxy-4-nitrobenzene and 900 mg (10.57 mmol) of cyclopropylmethylamine. Yield: 0.95 g (94% of theory); C14H20N2O4 (M=280.32); calc.: molecular ion peak (M+H)+: 281; found: molecular ion peak (M+H)+: 281; Rf value: 0.4 (silica gel, dichloromethane/methanol (9:1)).

Workup

  1. customPrepared analogously to Example 1.1.c

Sources & evidence

ORD record
ord-858480f0097245f98173d769349eb961
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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