Diisopropylethylamine → N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-2-oxoethanamine

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2.Br[CH2:17][C:18](Cl)=[O:19].[CH:21]([N:24](C(C)C)[CH2:25]C)(C)C>>[CH3:21][N:24]([CH3:25])[CH2:17][C:18]([N:8]1[CH2:7][CH2:6][C:5]2[C:10](=[CH:11][C:12]([N+:13]([O-:15])=[O:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:9]1)=[O:19]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 89602Bromoacetyl chloride

HCID 594418746-Methoxy-7-nitro-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 59441912N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-2-oxoethanamine

Procedure

A suspension of 6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (1.25 g, 6.00 mmol), bromoacetyl chloride (0.75 mL, 9.01 mmol), and polymer supported diisopropylethylamine (4.7 g, 18 mmol) was stirred for 4 hours, filtered, and taken to a residue under reduced pressure. The residue was redissolved in 2.0M methylamine in tetrahydrofuran (15 mL) and stirred overnight. The solution was concentrated under reduced pressure and purified by column chromatography to afford N,N-dimethyl-2-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-2-oxoethanamine as a mixture of apparent rotameric forms in DMSO (0.90 g, 3.07 mmol).