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

HRID 1014308Notes

Reaction equation

HRID 1014308 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

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 89602Bromoacetyl chlorideHCID 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).

Workup

  1. filtrationfiltered
  2. dissolutionThe residue was redissolved in 2.0M methylamine in tetrahydrofuran (15 mL)
  3. stirringstirred overnight
  4. concentrationThe solution was concentrated under reduced pressure
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-7ea67b788a25401eb8d0428926dec604
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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