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

HRID 1014355Notes

Reaction equation

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

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 2-acryloyl-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (0.8 g, 3 mmol) in methanol (10 mL) was treated with dimethyl amine (10 mL, 2 M in THF, 20 mmol, Aldrich) and heated at 65° C. in a sealed tube for 16 h. The mixture was cooled, concentrated, and partitioned between ethyl acetate and saturated aqueous ammonium chloride. The organic layer was separated, dried over magnesium sulfate, filtered, and purified by chromatography on SiO2 (dichloromethane to 20% methanol/dichloromethane) to give N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1 H)-isoquinolinyl]-3-oxo-1-propanamine (0.65 g, 71%). ESIMS (M+H)+=308.

Workup

temperatureThe mixture was cooled
concentrationconcentrated
custompartitioned between ethyl acetate and saturated aqueous ammonium chloride
customThe organic layer was separated
dry with materialdried over magnesium sulfate
filtrationfiltered
custompurified by chromatography on SiO2 (dichloromethane to 20% methanol/dichloromethane)

Sources & evidence

ORD record: ord-252c0847ab7340e696541b276f506630
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981903B2

Reaction notes

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