methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate → Methyl 4-{[2-(methylamino)ethyl]amino}benzoate

HRID 350557Notes

Reaction equation

HRID 350557 reaction equation
C(O[C:9]([N:11]([CH2:13][CH2:14][NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)C)=O)C1C=CC=CC=1>CO.[Pd]>[CH3:9][NH:11][CH2:13][CH2:14][NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 23511696methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate

Product 1

HCID 23512192Methyl 4-{[2-(methylamino)ethyl]amino}benzoateYield 78.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-[2-(N-benzyloxycarbonyl-N-methylamino)ethylamino]benzoate (1.26 g, 3.68 mmol) in MeOH(20 mL) was added 5 wt. Pd—C (700 mg), and the mixture was hydrogenated (3 atm) for 4 hr at room temp. The mixture was filtered, and the filtrate was evaporated under a reduced pressure to give 600 mg (78%) methyl 4-[2-(N-methylamino) ethylamino]benzoate as a colorless oil. 1H-NMR (CDCl3, 400 MHz) δ 2.46 (s, 3H), 2.88 (t, 2H, J=5.5 Hz), 3.27 (br s, 2H), 3.85 (s, 3H), 6.57 (d, 2H, J=8.8 Hz), 7.85 (d, 2H, J=8.8 Hz); MS (FAB) m/z 209 (M++1).

Workup

  1. customfor 4 hr
  2. customat room temp
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated under a reduced pressure

Sources & evidence

ORD record
ord-2f63c3f273cf4f0bb4d36b80e0941d59
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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