2-{3-[4-(1-Methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline → 2-{3-[4-(1-Methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine

HRID 1014360Notes

Reaction equation

HRID 1014360 reaction equation
[CH3:1][CH:2]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][CH2:11][C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([N+:26]([O-])=O)=[C:19]([O:24][CH3:25])[CH:20]=3)[CH2:15]2)=[O:13])[CH2:6][CH2:5]1)[CH3:3].[H][H]>C(O)C.[Pd]>[CH3:3][CH:2]([N:4]1[CH2:5][CH2:6][N:7]([CH2:10][CH2:11][C:12]([N:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][C:18]([NH2:26])=[C:19]([O:24][CH3:25])[CH:20]=3)[CH2:15]2)=[O:13])[CH2:8][CH2:9]1)[CH3:1]

Participants

5

Reactant 2

HCID 594417872-{3-[4-(1-Methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinolineHCID 178418361HCID 178418361, compound

Product 1

HCID 594417652-{3-[4-(1-Methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamineYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 2-{3-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-7-nitro-1,2,3,4-tetrahydroisoquinoline (285 g, 0.731 mmol) in ethanol (10 mL) was treated with 10% palladium on carbon (30 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-[4-(1-methylethyl)-1-piperazinyl]propanoyl}-6-(methyloxy)-1,2,3,4-tetrahydro-7-isoquinolinamine (0.26 g, 0.72 mmol, 99%). 1H NMR (400 MHz, DMSO-d6) is complicated due to amide rotomers δ ppm 0.92-0.98 (m, 6 H), 2.30-2.71 (m, some signals underneath DMSO, 15 H), 3.56-3.63 (m, 2 H), 3.72 (s, 3 H), 4.37-4.47 (two singlets at 4.38 and 4.45, 2 H), 4.53-4.59 (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), 6.55-6.58 (two singlets at 6.56 and 6.57, 1 H); ESIMS (M+H)+=361.

Workup

  1. customthe reaction vessel evacuated
  2. additionback-filled with nitrogen twice
  3. filtrationThe mixture was filtered through celite
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-331b85795e6646aeaf00ccb9856f233f
Source dataset
uspto-grants-2011_07
Patent number
US07981903B2

Reaction notes

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