N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-3-oxo-1-propanamine → 2-[3-(Dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine
Reaction equation
[CH3:1][N:2]([CH3:22])[CH2:3][CH2:4][C:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([N+:19]([O-])=O)=[C:12]([O:17][CH3:18])[CH:13]=2)[CH2:8]1)=[O:6].[H][H]>C(O)C.[Pd]>[CH3:22][N:2]([CH3:1])[CH2:3][CH2:4][C:5]([N:7]1[CH2:16][CH2:15][C:14]2[C:9](=[CH:10][C:11]([NH2:19])=[C:12]([O:17][CH3:18])[CH:13]=2)[CH2:8]1)=[O:6]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of N,N-dimethyl-3-[6-(methyloxy)-7-nitro-3,4-dihydro-2(1H)-isoquinolinyl]-3-oxo-1-propanamine (0.65 g, 2.1 mmol) in ethanol (10 mL) was treated with 10% palladium on carbon (70 mg, Aldrich), and stirred under 60 psi of hydrogen pressure for 16 h in a Fischer-Porter apparatus. The pressure was released, the reaction vessel evacuated, and back-filled with nitrogen twice. The mixture was filtered through celite and the filtrate was concentrated to provide 2-[3-(dimethylamino)propanoyl]-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (0.58 g, 2.1 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) is complicated due to amide rotomers d ppm 2.14 (s, 6 H), 2.46-2.52 (m, signals beneath DMSO, 4 H), 2.55-2.73 (m, two triplets at 2.58 and 2.69, 2 H), 3.58-3.63 (m, 2 H), 3.72 (s, 3 H), 4.37-4.48 (two singlets at 4.38 and 4.45, 2 H), 4.54-4.61 (two broad singlets at 4.55 and 4.58, 2 H), 6.38-6.42 (two singlets at 6.39 and 6.41, 1 H), 6.56-6.59 (two singlets at 6.56 and 6.57, 1 H); ESIMS (M+H)+=278.
Workup
- customthe reaction vessel evacuated
- additionback-filled with nitrogen twice
- filtrationThe mixture was filtered through celite
- concentrationthe filtrate was concentrated
Sources & evidence
- ORD record
- ord-ebfd72b4cab240cfad5ba33caca03804
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07981903B2
Reaction notes
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