Methylamine → 1-{3-[2-(2-Methoxyethoxy)ethoxy]phenyl}-2-(methylamino)ethanol

HRID 23657Notes

Reaction equation

HRID 23657 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]2[CH2:17][O:16]2)[CH:12]=[CH:13][CH:14]=1.[CH3:18][NH2:19]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][O:8][C:9]1[CH:10]=[C:11]([CH:15]([OH:16])[CH2:17][NH:19][CH3:18])[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 225743822-{3-[2-(2-Methoxyethoxy)ethoxy]phenyl}oxirane

Product 1

HCID 102146891-{3-[2-(2-Methoxyethoxy)ethoxy]phenyl}-2-(methylamino)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.78 g of 2-{3-[2-(2-methoxyethoxy)ethoxy]phenyl}oxirane in 30 ml of 2.0 M methylamine in methanol is stirred at room temperature overnight, then concentrated under reduced pressure. Flash chromatography of the residue on silica using 5-7% methanolic ammonia in CH2Cl2 affords 809 mg of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bb509f1b8640430d8cc33626b71a7076
Source dataset
uspto-grants-2005_02
Patent number
US06852731B2

Reaction notes

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